(+/-)-tert-butyl 1-(1-(methoxy(methyl)amino)-1-oxopropan-2-yl)-2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylate → HCID 89740938、化合物
反応式
CON(C)[C:4](=[O:24])[CH:5]([N:7]1[C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:10]2[C:9]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[C:8]1[CH3:23])[CH3:6].[CH3:26][Mg]Br>C1COCC1>[CH3:23][C:8]1[N:7]([CH:5]([C:4](=[O:24])[CH3:26])[CH3:6])[C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:10]2[C:9]=1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17]参加物
4
反応条件
- 温度
- 0 °C
実験手順
In a 50 mL round-bottom flask, under an atmosphere of N2, was added (±)-tert-butyl 1-(1-(methoxy(methyl)amino)-1-oxopropan-2-yl)-2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylate (0.630 g, 1.813 mmol) and THF (30 mL). The solution was cooled to 0° C. then methylmagnesium bromide (2.59 ml, 3.63 mmol) was added and the reaction was slowly warmed to ambient temperature while being monitored by LCMS. The reaction was done in 3 h at ambient temperature. Quenched with 50 mL 1N HCl, 50 mL brine, extracted with EtOAc, dried over Na2SO4, filtered, concentrated to provide (±)-tert-butyl 2-methyl-1-(3-oxobutan-2-yl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylate, which was used directly in the following reaction. LRMS (M+H+) m/z: calcd 303.37. found 303.1.