HCID 69349823、化合物 → 1-(4-chlorobenzyl)-5-(4-(2-hydroxypropan-2-yl)phenyl)pyridin-2(1H)-one
反応式
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][N:7]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([C:19](=[O:21])[CH3:20])=[CH:15][CH:14]=3)[CH:10]=[CH:9][C:8]2=[O:22])=[CH:4][CH:3]=1.[CH3:25][Mg]Br>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([OH:21])([CH3:25])[CH3:20])=[CH:15][CH:14]=3)[CH:10]=[CH:9][C:8]2=[O:22])=[CH:23][CH:24]=1参加物
4
反応条件
- 温度
- -50 °C
実験手順
According to Scheme 20: To a solution of 1-(4-chlorobenzyl)-5-(4-acetylphenyl)pyridin-2(1H)-one (1 eq, 0.20 mmol, 80 mg) in THF (5 mL) at −50° C. was added a solution of methyl magnesium bromide (3M, 1.3 eq, 0.30 mmol, 0.04 g) and the reaction stirred at −50° C. for 1 hour. The reaction was quenched at −78° C. with saturated aqueous NH4Cl. The reaction was allowed to warm to room temperature and diluted with AcOEt and the organic phase extracted (×3). The combined organic fractions were dried (Na2SO4), filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography over silica gel (AIT Flashsmart prepacked column 25 g SiO2) using CH2Cl2/AcOEt 80/20 and was recrystallized from pentane/Et2O to afford 1-(4-chlorobenzyl)-5-(4-(2-hydroxypropan-2-yl)phenyl)pyridin-2(1H)-one (0.08 mmol, 30 mg, 36%) as a white solid.