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

HRID 1095989Notes

Reaction equation

HRID 1095989 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.[CH3:25][O:26][C:27]1[CH:28]=[C:29](B(O)O)[CH:30]=[CH:31][C:32]=1[C:33]([O:35][CH3:36])=[O:34]>>[CH3:36][O:35][C:33]([C:32]1[CH:31]=[CH:30][C:29]([C:2]2[CH:7]=[CH:6][C:5]([CH:8]([CH3:23])[C:9]([OH:14])([C:15]3[CH:16]=[CH:17][C:18](=[O:22])[N:19]([CH3:21])[CH:20]=3)[C:10]([F:12])([F:11])[F:13])=[C:4]([Cl:24])[CH:3]=2)=[CH:28][C:27]=1[O:26][CH3:25])=[O:34]

Participants

3

Reactant 2

HCID 177502563-Methoxy-4-(methoxycarbonyl)benzeneboronic acidHCID 574213205-[2-(4-bromo-2-chloro-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-1-methyl-1H-pyridin-2-one

Product 1

HCID 667831423'-Chloro-3-methoxy-4'-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-propyl]-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-methyl-1H-pyridin-2-one (Example 165, step 3) was reacted with 3-methoxy-4-methoxycarbonylphenylboronic acid to give the title compound as an off-white solid. MS (m/e)=510.2 [M+H+].

Sources & evidence

ORD record
ord-dd2a7e059ab84cf5862b42b52afa4c59
Source dataset
uspto-grants-2012_03
Patent number
US08138189B2

Reaction notes

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