5-chloro-8-(2-fluorophenyl)-N-methoxy-N-methylquinoline-7-carboxamide → 1-[5-Chloro-8-(2-fluorophenyl)quinolin-7-yl]ethanone
Reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([C:12](N(OC)C)=[O:13])[C:9]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[F:24])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[CH3:25][Mg]Br>O1CCCC1>[Cl:1][C:2]1[CH:11]=[C:10]([C:12](=[O:13])[CH3:25])[C:9]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[F:24])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2Participants
4
Procedure
To a mixture of 5-chloro-8-(2-fluorophenyl)-N-methoxy-N-methylquinoline-7-carboxamide (40 mg, 0.1 mmol) in tetrahydrofuran (0.2 mL) was added 1.40 M methylmagnesium bromide in tetrahydrofuran (0.50 mL, 0.70 mmol). The reaction was stirred at room temperature overnight, quenched with saturated ammonium chloride, and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, and then concentrated to dryness under reduced pressure. The resultant residue was used directly in next step (32 mg, 92%). LCMS calculated for C17H12ClFNO(M+H)’ : m/z=300.1; found: 284.0.