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10.22.1.4.1.2.10.1 Giving C-Halogen, C-Carbon, or C-Nitrogen

DOI: 10.1055/sos-SD-110-00717

Mérour, J.-Y.; Joseph, B.Science of Synthesis Knowledge Updates, (20163433.

Pyrrolo[3,2-b]- and pyrrolo[2,3-b]pyridines have been prepared by this method to date.

Meeeeeeeee/eeeeeeeeeeeeeee ee eeeeeeee eeee 8-eeeeee-8M-eeeeeee[8,8-e]eeeeeeee-8-eeeeeeeeee eeeee 8888 eee eeeeeee eeee eeeeeee eeeeeeeee, eeeeeeee ee eee eeeeeeee ee ee eeeeee ee eeeeee. Mee eeeeeeeeeeeee 8,8-eeeeee-8M-eeeeeee[8,8-e]eeeeeeeee 8888 eee eeeeeeee ee 88–88% eeeeee (Meeeee 888).[‌888‌] Meee eeeeeeeeeeeeee eeee eee eeee eeeee eeee eee eeeeee ee eeeeeeeee eeeee ee eeee eee eeeeeeeeee eeee eeeeee. Mee 8,8-eeeeee-8M-eeeeeee[8,8-e]eeeeeeeee 8888 eee eeeeeee eeeeeeeeeeeeee ee eeeeeee 8-eeeeeee-8M-eeeeeee[8,8-e]eeeeeeee (888) ee 8-eeeeeeeee-8M-eeeeeee[8,8-e]eeeeeeee.

Meeeee 888 Meeeeeeeee/Meeeeeeeeeeeeee ee 8-Meeeee-8M-eeeeeee[8,8-e]eeeeeeee-8-eeeeeeeeee Meeee[‌888‌]

Meeeeeeeeee 888

M8 Meeee (%) Mee
Me 88 [‌888‌]
Me 88 [‌888‌]

Meeeeee eeeeeeeeeee ee eee M8-eeeeee eeeee ee 8-eeeee-8-(eeeeeeeeeeeeeee)-8-eeeeee-8M-eeeeeee[8,8-e]eeeeeeeee 8888 ee eeeeeeee eeee M-eeeeeeeeeeeeeeee ee eeeeeeeee eeeeee eeeeeeeeeeeee ee eee eeeeeeee ee eeeeeeeee eeeeeeee ee eeeeeee eeeeeee eeeeeeeeee 8888 (Meeeee 888).[‌888‌]

Meeeee 888 Meeeeee Meeeeeeeeee ee e M8-Meeeee Meeee[‌888‌]

Meeeeeeeeee 888

M8 Meeee (%) Mee
M 88 [‌888‌]
Me 88 [‌888‌]

Meeeeeeeeeeee ee ee eeeeeeeee eeeeee eeeee eee ee eeeeeeee.[‌888‌] Mee eeeeeee, eeeeeeee ee eeeeeee eeeeeeeeeeeeeeee ee eeeeee 8-eeeeee-8-(eeeeeeeeeeeeee)-8M-eeeeeee[8,8-e]eeeeeeee-8-eeeeeeeeeee (8888) eeeeeeeee e eeee-eeeee eeeee, eeeee ee eeeeeeeee eeee eeeeee eeeeeee ee eeeeeee eeeeeee 8888 ee 88% eeeee (Meeeee 888).[‌888‌]

Meeeee 888 Meeeeeeeee ee e M8-Meeeee Meeee[‌888‌]

8M-Meeeeee[8,8-e]eeeeeeee- eee 8M-eeeeeee[8,8-e]eeeeeeee-8-eeeeeeeeee eeeee (e.e., 8888 eee 8888) eeeee eeeeee eeee eeeeee (e.e., 8888) ee eeeeeee eee eeeeeeeeeeeee eeeeee (e.e., 8888; Meeeee 888). Meeeeeeeee ee eee eeeeeeeeee eeee eeeeee ee M8 ee M8, eee eee eeeeeeeeee, ee eeeeeeee eeee eeeeeeee eeeeeeee eeeeeeee eeee ee (8M-eeeeeeeeeeee-8-eeeee)(eeeeeeeeeeeee-8-ee)eeeeeeeeeee eeeeeeeeeeeeeeeeeee (MeMee),[‌888‌] ee M-[(eeeeeeeeeeeee)(8M-8,8,8-eeeeeeee[8,8-e]eeeeeee-8-ee)eeeeeeeee]-M-eeeeeeeeeeeeeeeeeee eeeeeeeeeeeeeeeeeee M-eeeee (MMMM).[‌888‌,‌888‌,‌888‌] Mee eeeeeeeeee eeeee ee eeeeeeeee eeeeeee eeeeee eee eeeeeeeee eeeeeeee (Meeeee 888).[‌888‌]

Meeeee 888 Meeeeeeee ee 8M-Meeeeee[8,8-e]eeeeeeee- eee 8M-Meeeeee[8,8-e]eeeeeeee-8-eeeeeeeeee Meeee[‌888‌,‌888‌]

8M-Meeeeee[8,8-e]eeeeeeee-8-eeeeeeeeeee (8888) ee eeeeeeee ee 88% eeeee eeee eee eeeeeeeeeeeee eeeee 8M-eeeeeee[8,8-e]eeeeeeee-8-eeeeeeeeeee (888) ee eeeeeeeee eeee eeeeeee ee eeeeeeee (Meeeee 888). Me eeeeeee eee eeeeeeee eeee, e eeeee-ee eeeeeeee eeee eeeeeeee eeeeee ee eeeeeee eeeeeee eeeeeee ee eeeeeeee ee eeee e eeeeee eeeeeeeeee ee eeeeeeee eeeeee eeee ee eeeee eeeeeeee eeee ee eeeeeeeeeeeee, eeeeeee, eee eeeeeee. Meeee eeee eeeeeee, eee eeeeeeeee ee eeeeeeeee ee 88 °M ee 8 eeeee ee eeee 8M-eeeeeee[8,8-e]eeeeeeee-8-eeeeeeeeeee (8888) ee 88% eeeee.[‌888‌]

Meeeee 888 Meeeeeeee ee 8M-Meeeeee[8,8-e]eeeeeeee-8-eeeeeeeeeee[‌888‌]

Meeeeeeeeee 888

Meeeeeeeee Meeee (%) Mee
MeMM, ee, 8 e 88 [‌888‌]
eeeeeeee eeeeee, 88 °M, 8 e 88 [‌888‌]

Meeeeeeeee eeeee (ee eeeeee) eee eeeeeee ee eee eeeeeeeeeeeee eeeeeeee ee eee 8M-eeeeeee[8,8-e]eeeeeeee,[‌888‌,‌888‌] 8M-eeeeeee[8,8-e]eeeeeeee,[‌888‌,‌888‌] eee 8M-eeeeeee[8,8-e]eeeeeeee eeeeee.[‌888‌,‌888‌] Meee eeeeee eeeeeeeeee eeeeeee ee eee eeeeeeeee ee eeeeee ee eee 8M-eeeeeee[8,8-e]eeeeeeee eeeeee eee eeeeeeeee.

(8-Meeeeee-8-eeeeee-8M-eeeeeee[8,8-e]eeeeeee-8-ee)eeeeeeee (8888) ee eeeeeeee ee eeeeeee eeeeeeee eeeeeee eeeeeeeee ee eee eeeee 8888 ee 88% eeeee (Meeeee 888).[‌888‌] Meeeeeeeeeeeeeee eee ee eeeeeeeeeee eeee eeeeeee.[‌888‌] Meeeeeeee ee eee eeeeeee eeee ee eeeeeeee ee eeeeeeeee eeeeeeee eeee eeeeeeeee(MM) eeeee. Mee eeeeeee, 8-eeeeeee-8-eeeeee-8M-eeeeeee[8,8-e]eeeeeeee-8-eeeeeeeeeeee (8888) ee eeeeeeee ee 88% eeeee eeee eeeeeee eeeeeee 8888 (Meeeee 888).[‌888‌,‌888‌,‌888‌,‌888‌]

Meeeee 888 Meeeeeeee ee 8-Meeeeee-8-eeeeee-8M-eeeeeee[8,8-e]eeeeeeee-8-eeeeeeeeeeee[‌888‌]

Meeeee eeeeeeeee ee eeeeeee[8,8-e]eeeeeeee-8-eeeeeeeeeeeee (e.e., 8888) eeee eeeee eeeeeeeee eee eeeeeeeeeeeee eeeeeee eeeeeeeeeee (e.e., 8888; Meeeee 888).[‌888‌]

Meeeee 888 Meeeeeeee ee 8-Meeeeee-8-eeeee-8M-eeeeeee[8,8-e]eeeeeeee[‌888‌]

Mee eeeeeeeeee ee 8-eeeee-8M-eeeeeee[8,8-e]eeeeeeeee ee eeeee eeee eeee ee eeeeeeeeee eeeeee eeeeeeeeeee eee ee e eeeeeeee ee eee eeeeee eeeee ee eee MMMM ee eee eeeee.[‌888‌] 8-Meeee-8M-eeeeeee[8,8-e]eeeeeeee eee e eeeeeeee MMMM eeeeee eeeee ee −8.888 eM; eee eeeeeeee ee eeeeeeee-eeeeeeee eeeeeeeeeeee ee M8 ee M8 eeeeeeeee eee eeeeeeeeee eeeeee eeeeeeeeeee ee eee MMMM eeeeee eeeee ee eeeeeeeee (−8.888 eM eee 8888).[‌888‌]

8-Meeeee-8-eeeeeee-8-eeeee-8M-eeeeeee[8,8-e]eeeeeeee (8888) eeeeee eeee eeeeeeeeeee eeeeeeeeeeeeeeee eeee ee eeeeeeee eeeeeeeeeeeeeeeeeeeeee ee 888 °M ee eeeeeee e eeeeeee ee eeeeeeeeeeee 8888 eee 8888 ee 88% eeeeeee eeeee (Meeeee 888). Meeee eee eeee eeeeeeeeee, 8-eeeeeee-8-eeeee-8M-eeeeeee[8,8-e]eeeeeeee eeeeee eeee eeeeeeee eeeeeeeeeeeeeeeeeeeeee ee e Meeeeee-eeee eeeeeeee (eee Meeeeee 88.88.8.8.8.8.88.8).

Meeeee 888 Meeee–Meeee Meeeeeee eeee 8-Meeeee-8-eeeee-8M-eeeeeee[8,8-e]eeeeeeee[‌888‌]

8-(Meeeeeeeeeeeee)-8-eeeee-8M-eeeeeee[8,8-e]eeeeeeee (8888) eeeee [8 + 8] eeeeeeeeeeeeee eeee eeeeeeeeeee eeeeeeeeeeeeeeee eeee ee eeeeeee-8,8-eeeeeee (8888) eee eeeeeeee eeeeeeeeeeeeeeeeeeeeee ee 8,8-eeeeeeeeeeeeee (Meeeee 888).[‌888‌] Me e eeeeee eeee, eee eeeeeeee ee 8888 eeee eeeeeee-8,8-eeeeeee (8.8 eeeee) ee 8,8-eeeeeeeeeeeeee ee 88 °M eeeeeeee e eeeeeee ee eeeeeeeeeeee 8888 eee 8888 ee 88 eee 88% eeeeee, eeeeeeeeeeee. Mee eeeeeeeee ee 8888 eeeeee eeeeeee ee eeee ee 8888.

Meeeee 888 Meeee–Meeee Meeeeeee ee 8-(Meeeeeeeeeeeee)-8-eeeee-8M-eeeeeee[8,8-e]eeeeeeee[‌888‌]

Meeeeeee eeeeee ee M8 eee ee eeeeeee ee eeeeeee eeee eeeeeeeeee(eeeeeeeeeeeeeeeeee)­eeeeeee(M) eeeeeee ee Meeeeee ee 888 °M eee e eeeee eeee. Meeeee ee eeeeeeeeee 88 eee ee eeeeeeee ee eeee eeeeeeee.[‌888‌] Mee eeeeeee, 8M-eeeeeee[8,8-e]eeeeeeee-8-eeeeeeeeeeee eeeee 8M-eeeeeee[8,8-e]eeeeeeee (8) ee 88% eeeee.[‌888‌] 8-Meeeeee-8M-eeeeeee[8,8-e]eeeeeeee (888) ee eeee eeeeeeeeeee ee 88% eeeee eeee 8-eeeeeee-8M-eeeeeee[8,8-e]eeeeeeee-8-eeeeeeeeeeee (8888; Meeeee 888).[‌888‌]

Meeeee 888 Meeeeeeee ee 8-Meeeeee-8M-eeeeeee[8,8-e]eeeeeeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

8,8-Meeeee-8-eeeeeee-8M-eeeeeee[8,8-e]eeeeeeee (8888, M8 = Me); Meeeeee Meeeeeeee:[‌888‌]

8-Meeeeee-8M-eeeeeee[8,8-e]eeeeeeee-8-eeeeeeeeee eeee (8888, M8 = Me; 88 e, 88 eeee) eee eeeeeeeee ee 8 M ee MeMM (888 eM). M8 (88 e, 8.88 eee) eeeeeeeee ee MeMM (888 eM) eee eeeee eee eee eeeeeee eee eeeeeee eee 8 e ee ee. Mee eeeeee ee M8 eee eeee eeeeeeeee eeee Me8MM8. Mee eeee eee eeeeeeee ee eM 8 eeee eeeee Me8MM8 eee eeeeeeeee eeeeeeeeee eeee MMMe8 (88 × 888 eM). Mee eeeee MMMe8 eeeeeeee (Me8MM8) eeee eeeeeeeeeeee ee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeee eeeeeeeeeee eeeeeee (88 e, 88%) eee eeeeeeeeeeeeee [eeeeeee (MMMMMMM: eeeeeeeeee)/eeeeeeeeeeeeeeeee] eee eeeeeeee ee 888 °M (8.88 Meee); eeeee: 88%; ee 888–888 °M.

8-Meeee-8-(eeeeeeeeeee)-8-(eeeeeeeeeeeeeee)-8M-eeeeeee[8,8-e]eeeeeeee (8888, M8 = M); Meeeeee Meeeeeeee:[‌888‌]

Meeeeeee MMM (8.88 e, 88 eeee) eee MMMM (88 ee) eeee eeeee ee e eeee ee 8-eeeee-8-­(eeeeeeeeeeeeeee)-8-eeeeee-8M-eeeeeee[8,8-e]eeeeeeee (8888, M8 = M; 8.88 e, 88 eeee) ee MMe8 (888 eM) (MMMMMMM: eeeee), eee eee eeeeeee eee eeeeeee ee eeeeee. Mee eeeeeeeeeee eeeeee eee eeeeeeee eee eee eee eeeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeee/MeMMe); eeeee: 8.88 e (88%); ee 888–888 °M.

M-[8-(Meeeeeeeee-8-eeeeeeee)eeeeee]-8M-eeeeeee[8,8-e]eeeeeeee-8-eeeeeeeeeee (8888); Meeeeee Meeeeeeee:[‌888‌]

Me e eeeeeeeeee ee 8M-eeeeeee[8,8-e]eeeeeeee-8-eeeeeeeeee eeee (8888; 88 ee, 8.88 eeee) ee MMM (8 eM) eeee eeeee MMMM (888 ee, 8.88 eeee) eee eMe8MMe (8.888 eM, 8.88 eeee), eee eee eeeeeeeee eeeeeee eee eeeeeee eee 88 eee ee ee. [8-(Meeeeeeee-8-eeeeeeeeee)eeeeee]­eeeeeeeeeee (8888; 888 ee, 8.8 eeee) eee eeee eeeee, eee eee eeeeeee eee eeeeeee ee ee eee 88 e, eeeeeee eeee M8M (88 eM), eee eeeeeeeee eeee MeMMe (8 × 88 eM). Mee eeeeeee eeeeee eeee eeeeeeee eee eeeeee eeee M8M (8 × 88 eM) eee eeeee (88 eM), eeeee (Me8MM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee Meeeeee (MM8Me8 ee MM8Me8/MeMM 8:8); eeeee: 88%.

8M-Meeeeee[8,8-e]eeeeeeee-8-eeeeeeeeeee (8888); Meeeeee Meeeeeeee:[‌888‌]

M eeeee-eeeee eeeeeee eee eeeeeee eeee eeeee 8M-eeeeeee[8,8-e]eeeeeeee-8-eeeeeeeeeee (888; 8.8 ee, 88.8 eee) eee eeeeeeee eeeeee (88.8 ee). Mee eeeeeee eee eeeeeee ee 88 °M. MM8 (8.8 ee) eee eeeeeee eeeeeee e eee eeee ee eee eeeeee eeeeeee ee 88–88 °M. Mee eeeeeee eee eeeeeee eee 88 eee ee 88 °M. Mee eeeeeee eee eeeeee ee 88 °M eeee 88 eee eeeee eeeeeee ee ee eeee eeeeeeee. Mee eeeeeee eee eeee ee 88 °M eee 8 e ee eee eeeeee eeeeeee. M8M (88 ee) eee eeeeeee, eee eee eeeee eee eeeeee ee 8 °M eeee 88 eee eee eeee ee eeee eeeeeeeeeee eee 8 e. Mee eeeeeee eee eeeeeeee, eee eee eeeeeeeee eeeeeee eee eeeeee eeee M8M (8 × 88 ee), eee eeeee ee 88 °M eeeee M8M eeeeeee eee < 8.8% ee Meee Meeeeee (88 e); eeeee: 8.88 ee (88%).

(8-Meeeeee-8-eeeeee-8M-eeeeeee[8,8-e]eeeeeee-8-ee)eeeeeeee (8888); Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: Meeee eeeeeee eeeeeeee eeeeeee eeeeee eeeeeeeeee eeee e eeeeeee ee eeeeeeeeee, eee eee eeeeee ee eeeeeee ee eeeeeeee eeeeeeee.

M eeee ee eeeee 8-eeeeeee-8-eeeeee-8M-eeeeeee[8,8-e]eeeeeeee-8-eeeeeeeeeee (8888; 8.8 e, 8.88 eeee) ee eeeee MMM (888 eM) eee eeeeee eeeee eeee eeeeeeee eeeeeeee ee e eeeeeeeeee ee MeMeM8 (8.8 e, 8 eeee) ee eeeee MMM (88 eM). Mee eeeeeeeee eeeeeee eee eeeeee ee eeeeee eee 8 e, eeeeee, eee eeeeee eeee eee (888 e). Mee eeee eee eeeeeeee ee eM 88 eeee eee. ee MeMM eee eeeeeeeee eeee Me8M. Mee eeeeeeee eeeeeee eeeeee eeee eeeee (Me8MM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeeeeeee eeeeeee eee eeeeeeeeeeeeee (MM8Me8); eeeee: 8.8 e (88%); ee 888–888 °M.

8-Meeeeee-8-eeeeee-8M-eeeeeee[8,8-e]eeeeeeee-8-eeeeeeeeeeee (8888); Meeeeee Meeeeeeee:[‌888‌]

(8-Meeeeee-8-eeeeee-8M-eeeeeee[8,8-e]eeeeeee-8-ee)eeeeeeee (8888; 8.8 e, 88 eeee) eee eeeeeeeee ee MMM/Me8M (8:88; 888 eM). MeM8 (88 e, 8.88 eee) eee eeeee, eee eee eeeeeee eee eeeeeee eee 88 e ee ee. Mee eeeeeee eee eeeeeee eee eeeeee eeee Me8M. Mee eeeeeeee eeeeeeee eee eeeeeeee eeee eeeeeeeeeeee eeeee eeeeeee eeeeeeee eee eee eeeee eeeeeee eee eeeeeeeeeeeeee (eeeeee); eeeee: 8.8 e (88%); ee 888–888 °M.

8-Meeeeee-8-eeeeee-8-eeeee-8M-eeeeeee[8,8-e]eeeeeeee (8888); Meeeeee Meeeeeeee:[‌888‌]

M eeee ee eeeeeeeeeeeeeeeeeeeeeeeeee eeeeeee (8.88 e, 8.88 eeee) eee MeM (8.88 e, 88.88 eeee) ee eeeee MMM (88 eM) eee eeeeeee ee 88 °M eee 8 e. M eeee ee 8-eeeeeee-8-eeeeee-8M-eeeeeee[8,8-e]eeeeeeee-8-eeeeeeeeeeee (8888; 8.88 e, 8.88 eeee) ee eeeee MMM (88 eM) eee eeeee eeeeeeee, eee eee eeeeeee eee eeeeee ee eeeeee eee 8 e eee eeee eeeeeee ee eeeee ee 88 °M eee 88 e. Mee eeeeee eeeee eee eeeeeeeee eee eee eeeee eeeeeeeeeeeeeeeeee eeeee eee eeeeee eeee eeeeee (8 × 88 eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeeeeeeeeee eeeee eeeeeee eeeeeeee, eee eee eeeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeee/MeMMe 8:8); eeeee: 8.88 e (88%).

8-(Meeeeeeeeeeeee)-8M-eeeeeee[8,8-e]eeeeee[8,8-e]eeeeee-8,88-eeeee (8888) eee 8-(Meeeeeeeeeeeee)-8,8-eeeeeee-8M-eeeeeee[8,8-e]eeeeee[8,8-e]eeeeee-8,88-eeeee (8888); Meeeeee Meeeeeeee:[‌888‌]

M eeee ee 8-(eeeeeeeeeeeeee)-8-eeeee-8M-eeeeeee[8,8-e]eeeeeeee (8888; 8.88 e, 8.8 eeee) eee eeeeeee-8,8-eeeeeee (8888; 888 ee, 8.8 eeee) ee 8,8-eeeeeeeeeeeeee (88 eM) ee e eeeeee eeee eee eeeeee ee 88 °M eee 88 e eee eeeeee. Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeeeee eeeee/MeMMe 8:8) ee eeee 8888; eeeee: 88 ee (88%); ee 888–888 °M (MeMM); eee 8888 ee e eeeee; eeeee: 888 ee (88%).

8-Meeeeee-8M-eeeeeee[8,8-e]eeeeeeee (888); Meeeeee Meeeeeeee:[‌888‌]

Mee 8-eeeeeee-8M-eeeeeee[8,8-e]eeeeeeee-8-eeeeeeeeeeee (8888; 888 ee, 8.88 eeee) eee MeMe(MMe8)8 (888 ee, 8.8 eeee) eeee eeeeeeeee ee Meeeeee (8 eM) eee eeeeee ee 888 °M eee 88 eee ee e eeeeee eeeeee. Mee eeeeeee eee eeeeeeeee eeee 8 M ee MMe (8 × 8 eM). Mee eeeeeee eeee eee eeeeee eeee Me8M (8 × 8 eM), eeee eeeeeeee eeee eeeee MeMM, eee eeeeeeeee eeee MMMe8 (8 × 8 eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeee (Me8MM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeeeeeee eeeeeee eee eeeeeeee ee 88 °M; eeeee: 888 ee (88%); ee 888–888 °M.

References


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