4-(Cyanomethyl)benzeneboronic acid → {3'-Chloro-4'-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-propyl]-biphenyl-4-yl}-acetonitrile

HRID 1095987Notes

Reaction equation

HRID 1095987 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:23])[C:9]([C:15]2[CH:16]=[CH:17][C:18](=[O:22])[N:19]([CH3:21])[CH:20]=2)([OH:14])[C:10]([F:13])([F:12])[F:11])=[C:4]([Cl:24])[CH:3]=1.[C:25]([CH2:27][C:28]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=1)#[N:26]>>[Cl:24][C:4]1[CH:3]=[C:2]([C:31]2[CH:32]=[CH:33][C:28]([CH2:27][C:25]#[N:26])=[CH:29][CH:30]=2)[CH:7]=[CH:6][C:5]=1[CH:8]([CH3:23])[C:9]([OH:14])([C:15]1[CH:16]=[CH:17][C:18](=[O:22])[N:19]([CH3:21])[CH:20]=1)[C:10]([F:13])([F:12])[F:11]

Participants

3

Reactant 2

HCID 27733424-(Cyanomethyl)benzeneboronic acidHCID 574213205-[2-(4-bromo-2-chloro-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-1-methyl-1H-pyridin-2-one

Product 1

HCID 66782267{3'-Chloro-4'-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-propyl]-biphenyl-4-yl}-acetonitrile

Procedure

In analogy to Example 150, step 2, 5-[2-(4-bromo-2-chloro-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-1-methyl-1H-pyridin-2-one (Example 165, step 3) was reacted with 4-cyanomethylphenylboronic acid to give the title compound as an off-white solid. MS (m/e)=461.3 [M+H+].

Sources & evidence

ORD record
ord-87152c9b79814fbdb1bb5a0fb381170b
Source dataset
uspto-grants-2012_03
Patent number
US08138189B2

Reaction notes

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