Aniline → Phenylamino-(4-trifluoromethyl-phenyl)-acetic acid ethyl ester

HRID 77026Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:21])[CH:5](OS(C)(=O)=O)[C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][CH:7]=1)[CH3:2].[NH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.CCN(C(C)C)C(C)C>C(#N)C>[CH2:1]([O:3][C:4](=[O:21])[CH:5]([NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][CH:7]=1)[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

Methanesulfonyloxy-(4-trifluoromethyl-phenyl)-acetic acid ethyl ester (I102) (594 mg, 1.82 mmol), aniline (0.25 mL, 2.73 mmol), and DIPEA (0.48 mL, 2.73 mmol) are dissolved in acetonitrile (4 mL). The reaction is heated under microwave irradiation at 100° C. for 1 hour and 30 minutes. Aniline (0.17 mL, 1.820 mmol) is added again and the reaction is heated under microwave irradiation at 100° C. for 3 hours. Acetonitrile is removed under vacuum and the residue is purified by flash chromatography (Petroleum ether/DCM=75/25) to afford intermediate I151 as a yellow oil (195 mg, 60% yield).

Workup

temperaturethe reaction is heated under microwave irradiation at 100° C. for 3 hours
customAcetonitrile is removed under vacuum
customthe residue is purified by flash chromatography (Petroleum ether/DCM=75/25)

Sources & evidence

ORD record: ord-8545127f95aa4575b0973415b8ec7e40
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835682B2

Reaction notes

Loading…