2-Fluoro-5-methylbenzeneboronic acid → Methyl 2-(1-(5-(2-fluoro-5-methylphenyl)pyrimidin-2-yl)-N-methyl-3-(methylthio)-1H-indole-6-carboxamido)acetate

HRID 630533Notes

Reaction equation

HRID 630533 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]([N:19]([CH2:21][C:22]([O:24][CH3:25])=[O:23])[CH3:20])=[O:18])[CH:15]=3)[C:10]([S:26][CH3:27])=[CH:9]2)=[N:6][CH:7]=1.[F:28][C:29]1[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][C:30]=1B(O)O>>[F:28][C:29]1[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][C:30]=1[C:2]1[CH:3]=[N:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]([N:19]([CH2:21][C:22]([O:24][CH3:25])=[O:23])[CH3:20])=[O:18])[CH:15]=3)[C:10]([S:26][CH3:27])=[CH:9]2)=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 103518842-Fluoro-5-methylbenzeneboronic acidHCID 118666033Methyl 2-(1-(5-bromopyrimidin-2-yl)-N-methyl-3-(methylthio)-1H-indole-6-carboxamido)acetate

Product 1

HCID 118666155Methyl 2-(1-(5-(2-fluoro-5-methylphenyl)pyrimidin-2-yl)-N-methyl-3-(methylthio)-1H-indole-6-carboxamido)acetate

Procedure

Suzuki coupling of 304a) (0.5 g, 1.11 mmol) and (2-fluoro-5-methylphenyl)boronic acid (0.34 g, 2.22 mmol) under use of (Ataphos)2PdCl2 (79 mg, 0.11 mmol) as catalyst analogously to the protocol for example 261. White solid. Yield: 0.51 g (96% of theory)

Sources & evidence

ORD record
ord-8c79370156e84fefb0e8442bc1e92b30
Source dataset
uspto-grants-2016_04
Patent number
US09315490B2

Reaction notes

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