3-Chloro-4-fluorophenylboronic Acid (contains varying amounts of Anhydride) → 4-Hydroxy-4'-trifluoromethyl-biphenyl-3-carboxylic acid [2-(3'-chloro-4'-fluoro-6-methoxy-biphenyl-3-yl)-ethyl]-amide

HRID 2373792Notes

Reaction equation

HRID 2373792 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)=[CH:4][C:3]=1[C:18]([OH:20])=O.Br[C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][C:30]=1[O:31][CH3:32])[CH2:25][CH2:26][NH2:27].[Cl:33][C:34]1[CH:35]=[C:36](B(O)O)[CH:37]=[CH:38][C:39]=1[F:40]>>[Cl:33][C:34]1[CH:35]=[C:36]([C:22]2[C:30]([O:31][CH3:32])=[CH:29][CH:28]=[C:24]([CH2:25][CH2:26][NH:27][C:18]([C:3]3[CH:4]=[C:5]([C:8]4[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=4)[CH:6]=[CH:7][C:2]=3[OH:1])=[O:20])[CH:23]=2)[CH:37]=[CH:38][C:39]=1[F:40]

Participants

4

Reactant 3

HCID 27346603-Chloro-4-fluorophenylboronic Acid (contains varying amounts of Anhydride)HCID 27355812-(3-Bromo-4-methoxyphenyl)ethan-1-amineHCID 27827012-hydroxy-5-[4-(trifluoromethyl)phenyl]benzoic Acid

Product 1

HCID 112497504-Hydroxy-4'-trifluoromethyl-biphenyl-3-carboxylic acid [2-(3'-chloro-4'-fluoro-6-methoxy-biphenyl-3-yl)-ethyl]-amideYield 24.5%

Procedure

The resin-bound 4-hydroxy-4′-trifluoromethyl-biphenyl-3-carboxylic acid (20 mg, 0.06 mmol) obtained as in Example 1 was reacted with 3-bromo-4-methoxy-phenethyl amine (57 mg, 0.25 mmol) following general procedure A to give resin bound 4-Hydroxy-4′-trifluoromethyl-biphenyl-3-carboxylic acid [2-3-bromo-4-methoxy-phenyl)-ethyl]-amide(18 mg, 0.05 mmol). The above resin bound amide was treated with 3-chloro-4-fluoro-phenyl boronic acid (43 mg, 0.25 mmol) as described in the general procedure D to provide the title compound (8.0 mg,).

Workup

  1. customto give resin

Sources & evidence

ORD record
ord-4c7e4a753f2a40db88c296372a7c3f7b
Source dataset
uspto-grants-2008_12
Patent number
US07459472B2

Reaction notes

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