3-Methoxy-4-(methoxycarbonyl)benzeneboronic acid → 3'-Chloro-4'-[2-(1-ethyl-6-oxo-1,6-dihydro-pyridin-3-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-3-methoxy-biphenyl-4-carboxylic acid methyl ester

HRID 1096005Notes

Reaction equation

HRID 1096005 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:24])[C:9]([C:15]2[CH:16]=[CH:17][C:18](=[O:23])[N:19]([CH2:21][CH3:22])[CH:20]=2)([OH:14])[C:10]([F:13])([F:12])[F:11])=[C:4]([Cl:25])[CH:3]=1.[CH3:26][O:27][C:28]1[CH:29]=[C:30](B(O)O)[CH:31]=[CH:32][C:33]=1[C:34]([O:36][CH3:37])=[O:35]>>[CH3:37][O:36][C:34]([C:33]1[CH:32]=[CH:31][C:30]([C:2]2[CH:7]=[CH:6][C:5]([CH:8]([CH3:24])[C:9]([C:15]3[CH:16]=[CH:17][C:18](=[O:23])[N:19]([CH2:21][CH3:22])[CH:20]=3)([OH:14])[C:10]([F:11])([F:13])[F:12])=[C:4]([Cl:25])[CH:3]=2)=[CH:29][C:28]=1[O:27][CH3:26])=[O:35]

Participants

3

Reactant 2

HCID 177502563-Methoxy-4-(methoxycarbonyl)benzeneboronic acidHCID 574213235-[2-(4-Bromo-2-chloro-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-1-ethyl-1H-pyridin-2-one

Product 1

HCID 667826903'-Chloro-4'-[2-(1-ethyl-6-oxo-1,6-dihydro-pyridin-3-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-3-methoxy-biphenyl-4-carboxylic acid methyl ester

Procedure

In analogy to Example 150, step 2, 5-[2-(4-bromo-2-chloro-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-1-ethyl-1H-pyridin-2-one (Example 183, step 2) was reacted with 3-methoxy-4-methoxycarbonylphenylboronic acid to give the title compound as an off-white solid. MS (m/e)=524.2 [M+H+].

Sources & evidence

ORD record
ord-27a9d8e2e98440bbaaa97e09defd4a7d
Source dataset
uspto-grants-2012_03
Patent number
US08138189B2

Reaction notes

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