Methyl 2-amino-5-bromobenzoate → HCID 68867662, compound

HRID 2373793Notes

Reaction equation

HRID 2373793 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8](Br)[CH:7]=[CH:6][C:5]=1[NH2:11].[F:13][C:14]([F:25])([F:24])[C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.[CH3:26][O:27][C:28](=[O:46])[C@@H:29]([NH2:45])[CH2:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]2[CH:42]=[CH:41][C:40]([F:43])=[C:39]([Cl:44])[CH:38]=2)=[CH:33][CH:32]=1>>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[C:8]([C:18]2[CH:19]=[CH:20][C:15]([C:14]([F:25])([F:24])[F:13])=[CH:16][CH:17]=2)[CH:7]=[CH:6][C:5]=1[NH2:11])=[O:12].[CH3:26][O:27][C:28](=[O:46])[C@@H:29]([NH:45][C:3]([C:4]1[CH:9]=[C:8]([C:18]2[CH:19]=[CH:20][C:15]([C:14]([F:25])([F:24])[F:13])=[CH:16][CH:17]=2)[CH:7]=[CH:6][C:5]=1[NH2:11])=[O:12])[CH2:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]2[CH:42]=[CH:41][C:40]([F:43])=[C:39]([Cl:44])[CH:38]=2)=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 736224Methyl 2-amino-5-bromobenzoateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 68869262HCID 68869262, compound

Product 2

HCID 11273104HCID 11273104, compoundHCID 68867662HCID 68867662, compoundYield 1,016.1%

Procedure

4-Amino-4′-trifluoromethyl-biphenyl-3-carboxylic acid methyl ester (3.0 g) was prepared from 2-amino-5-bromobenzoic acid methyl ester (4.58 g, 20 mmol) and 4-trifluoromethylphenyl boronic acid (4.75 g, 25 mmol) following general procedure D, then hydrolyzed following general procedure C. The above acid (281 mg, 1.0 mmol) was reacted with 2(S)-amino-3-(3′chloro-4′-fluoro-biphenyl-4-yl)-propionic acid methyl ester (343 mg, 1.0 mmol) as described in general procedure A to give the title compound. (300 mg)

Sources & evidence

ORD record
ord-1e47c9ca161d47cab1a0d99c75f5c073
Source dataset
uspto-grants-2008_12
Patent number
US07459472B2

Reaction notes

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