Ethyl Acetate → N-(6-Chloro-3-pyridinyl)-3-(trifluoromethyl)benzamide
Reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:8])=[N:6][CH:7]=1.C(N(CC)C(C)C)(C)C.[F:18][C:19]([F:30])([F:29])[C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][CH:28]=1)[C:23](Cl)=[O:24].C(OCC)(=O)C>C(#N)C>[Cl:8][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:23](=[O:24])[C:22]2[CH:26]=[CH:27][CH:28]=[C:20]([C:19]([F:18])([F:29])[F:30])[CH:21]=2)=[CH:7][N:6]=1Participants
6
Conditions
- Temperature
- 55 °C
Procedure
To a stirring solution of 5-amino-2-chloropyridine (129 mg, 1 mmol) and N,N-diisopropylethylamine (209 μL, 1.2 mmol) in dry acetonitrile (5 mL) was added 3-(trifluoromethyl)benzoyl chloride (151 μL, 1 mmol). The resulting solution was heated at 55° C. for 3h. After cooling to room temperature ethyl acetate (10 mL) was added and the solution was washed with water (2×10 mL) and dried (Na2SO4). The solvent was removed under reduced pressure and the crude material was purified by column chromatography (4:1, hexane/ethyl acetate) to afford the desired product as a white solid (284 mg, 94%).
Workup
- additionwas added
- washthe solution was washed with water (2×10 mL)
- dry with materialdried (Na2SO4)
- customThe solvent was removed under reduced pressure
- customthe crude material was purified by column chromatography (4:1, hexane/ethyl acetate)
Sources & evidence
- ORD record
- ord-b89e1df15a884f8da8ff400dcb0cc5a0
- Source dataset
- uspto-grants-2002_04
- Patent number
- US06372767B1
Reaction notes
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