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

HRID 1095999Notes

Reaction equation

HRID 1095999 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:23])[C:9]([C:15]2[CH:16]=[N:17][C:18]([O:21][CH3:22])=[CH:19][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]=[N:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=1)[C:10]([F:13])([F:12])[F:11]

Participants

3

Reactant 2

HCID 27733424-(Cyanomethyl)benzeneboronic acidHCID 574213213-(4-Bromo-2-chloro-phenyl)-1,1,1-trifluoro-2-(6-methoxy-pyridin-3-yl)-butan-2-ol

Product 1

HCID 66699162{3'-Chloro-4'-[3,3,3-trifluoro-2-hydroxy-2-(6-methoxy-pyridin-3-yl)-1-methyl-propyl]-biphenyl-4-yl}-acetonitrile

Procedure

In analogy to Example 150, step 2, 3-(4-bromo-2-chloro-phenyl)-1,1,1-trifluoro-2-(6-methoxy-pyridin-3-yl)-butan-2-ol (Example 175, step 3) was reacted with 4-cyanomethylphenylboronic acid to give the title compound as a colorless foam. MS (m/e)=461.3 [M+H+]

Sources & evidence

ORD record
ord-7af333152bcd4acd9d69bc185f36b741
Source dataset
uspto-grants-2012_03
Patent number
US08138189B2

Reaction notes

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