Pyridine → 4-fluoro-N,N-bis(4-methoxyphenyl)-2-(trifluoromethyl)benzamide

HRID 1486395Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[CH:5][CH:4]=1.[F:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[C:21]([C:28]([F:31])([F:30])[F:29])[CH:20]=1.N1C=CC=CC=1>C1COCC1>[F:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([N:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[O:24])=[C:21]([C:28]([F:29])([F:30])[F:31])[CH:20]=1

Participants

Conditions

Temperature: 90 °C

Procedure

1 equivalent of bis-(4-methoxyphenyl)amine (1a) (0.73 g, 3.18 mmol) was mixed with 1.2 equivalents of 4-fluoro-2-trifluoromethylbenzoyl chloride (0.87 g, 3.82 mmol) and 6 equivalents of pyridine (1.51 g, 19.08 mmol) in a dry three-necked round-bottomed flask equipped with a magnetic stirring bar and a reflux condenser. The mixture was dissolved in anhydrous THF (20 mL) and heated to 90° C. for 20 hours. The reaction solution was cooled to room temperature and filtered. The solvent was removed under reduced pressure. The residue was purified by flash column chromatography using silica-gel with EtOAc/hexanes (3/7 v/v) to afford the pure corresponding benzamide compound as a colorless oil, 1.12 g, 84.2% yield. 1H NMR (CDCl3, 300 MHz) δ 7.34-7.26 (m, 4H), 7.09-7.01 (m, 3H), 6.91 (d, 2H, J=8.7 Hz), 6.87 (d, 2H, J=8.7 Hz), 3.80 (s, 3H), 3.71 (s, 3H). MS m/z 442.1 (M+Na)+.

Workup

customequipped with a magnetic stirring bar and a reflux condenser
temperatureThe reaction solution was cooled to room temperature
filtrationfiltered
customThe solvent was removed under reduced pressure
customThe residue was purified by flash column chromatography

Sources & evidence

ORD record: ord-eee7c3af641e4c93a0ecb1d22e442f31
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09427418B2

Reaction notes

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