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10.24.3.2.1.2.1 Substitution of Bromide with Aryl

DOI: 10.1055/sos-SD-110-02000

Harris, P. A.Science of Synthesis Knowledge Updates, (20213141.

Methyl 5-bromopyrimido[1,6-a]indole-3-carboxylate (105) undergoes palladium-catalyzed arylation or hetarylation with either (het)arylboronic acids or -tributylstannanes to furnish methyl 5-(het)arylpyrimido[1,6-a]indole-3-carboxylates 106 and 107, respectively (Scheme 31).[‌30‌] Suzuki coupling of aryl- and electron-rich hetarylboronic acids gives higher yields than those obtained using Stille reaction of the corresponding aryl- and hetaryl(tributyl)stannanes. In contrast, the Stille reaction with electron-poor hetaryl(tributyl)stannanes gives low yields, but better results than electron-poor boronic acids, which do not react.

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Me8 Meeee (%) Mee
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8-MeMM8M8 88 [‌88‌]
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Me8 Meeee (%) Mee
8-eeeeeee 88 [‌88‌]
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