3,4,5-Trifluoroaniline → (3-Fluoro-phenyl)-(3,4,5-trifluoro-phenylamino)-acetic acid methyl ester

HRID 453687Notes

Reaction equation

Br[CH:2]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[CH:8]=1)[C:3]([O:5][CH3:6])=[O:4].[F:14][C:15]1[CH:16]=[C:17]([CH:19]=[C:20]([F:23])[C:21]=1[F:22])[NH2:18]>C(#N)C>[CH3:6][O:5][C:3](=[O:4])[CH:2]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[CH:8]=1)[NH:18][C:17]1[CH:16]=[C:15]([F:14])[C:21]([F:22])=[C:20]([F:23])[CH:19]=1

Participants

Conditions

Temperature: 120 °C

Procedure

Methyl 2-bromo-2-(3-fluorophenyl)acetate (300 mg, 1.21 mmol) and 3,4,5-trifluoroaniline (268 mg, 1.82 mmol) were dissolved in acetonitrile (4 ml) and stirred under microwave heating into a sealed vial at 120° C. for 1 hours. Some crystals of KI were added, and the resulting mixture was stirred under the same conditions for 1 hour (UPLC-MS: conversion complete). Solvent was evaporated, and the crude residue was purified by flash chromatography (Petroleum ether/EtOAc=9/1) to obtain (3-fluoro-phenyl)-(3,4,5-trifluoro-phenylamino)-acetic acid methyl ester (202 mg, 53% yield).

Workup

additionSome crystals of KI were added
stirringthe resulting mixture was stirred under the same conditions for 1 hour (UPLC-MS: conversion complete)
customSolvent was evaporated
customthe crude residue was purified by flash chromatography (Petroleum ether/EtOAc=9/1)

Sources & evidence

ORD record: ord-f467f5d9d7a84074b2071bbd25ecda4c
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492548B2

Reaction notes

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