1-(1-Butoxy-9-fluorobenzo[c]-1,6-naphthyridin-6-yl)ethanone → 2-(1-Butoxy-9-fluorobenzo[c]-1,6-naphthyridin-6-yl)propan-2-ol
Reaction equation
[CH2:1]([O:5][C:6]1[N:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[C:8]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:9]=1[C:10]([C:16](=[O:18])[CH3:17])=[N:11]2)[CH2:2][CH2:3][CH3:4].[CH3:24][Mg]Br>O1CCCC1>[CH2:1]([O:5][C:6]1[N:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[C:8]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:9]=1[C:10]([C:16]([OH:18])([CH3:24])[CH3:17])=[N:11]2)[CH2:2][CH2:3][CH3:4]Participants
4
Procedure
To a stirred solution of 1-(1-butoxy-9-fluorobenzo[c]-1,6-naphthyridin-6-yl)ethanone (59 mg, 0.19 mmol) in tetrahydrofuran (2.0 ml) was added methylmagnesium bromide (1.4 M in toluene/THF 75:25; 0.202 ml, 0.283 mmol) dropwise at −78° C. The cooling bath was removed, and the resulting suspension was allowed to warm to room temperature. The reaction mixture was stirred for 30 minutes, and then quenched with saturated aqueous ammonium chloride (5 mL). Water was added, and the mixture extracted with EtOAc. The organic layer was dried over sodium sulfate, filtered and concentrated to a crude solid that was adsorbed on to silica gel and purified by column chromatography on silica gel eluting with an EtOAc/hexanes gradient to afford 2-(1-butoxy-9-fluorobenzo[c]-1,6-naphthyridin-6-yl)propan-2-ol. LRMS (ESI) calc'd for (C19H21FN2O2) [M+H]+, 329.2; found 329.1.