3-(Ethoxycarbonyl)-4-fluorophenylboronic Acid (contains varying amounts of Anhydride) → 3'-Chloro-4-fluoro-4'-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-propyl]-biphenyl-3-carboxylic acid ethyl ester

HRID 1095988Notes

Reaction equation

HRID 1095988 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.[F:25][C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][C:27]=1[C:35]([O:37][CH2:38][CH3:39])=[O:36]>>[CH2:38]([O:37][C:35]([C:27]1[CH:28]=[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:11])([F:12])[F:13])=[C:4]([Cl:24])[CH:3]=2)[CH:30]=[CH:31][C:26]=1[F:25])=[O:36])[CH3:39]

Participants

3

Reactant 2

HCID 249017713-(Ethoxycarbonyl)-4-fluorophenylboronic Acid (contains varying amounts of Anhydride)HCID 574213205-[2-(4-bromo-2-chloro-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-1-methyl-1H-pyridin-2-one

Product 1

HCID 666991203'-Chloro-4-fluoro-4'-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-propyl]-biphenyl-3-carboxylic acid ethyl 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 4-fluoro-3-ethoxycarbonylphenylboronic acid to give the title compound as a colorless foam. MS (m/e)=512.4 [M+H+].

Sources & evidence

ORD record
ord-be4210e6423b415890fdc2db1151f6ec
Source dataset
uspto-grants-2012_03
Patent number
US08138189B2

Reaction notes

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