Dimethylformamide → 5-Fluoro-3-methyl-pyrrolo[3,2-b]pyridin-1-ylamine
반응식
[F:1][C:2]1[N:7]=[C:6]2[C:8]([CH3:11])=[CH:9][NH:10][C:5]2=[CH:4][CH:3]=1.[H-].[Na+].C[N:15](C=O)C>>[F:1][C:2]1[N:7]=[C:6]2[C:8]([CH3:11])=[CH:9][N:10]([NH2:15])[C:5]2=[CH:4][CH:3]=1참가 물질
4
반응 조건
- 온도
- 0 °C
실험 절차
A solution of 5-fluoro-3-methyl-1H-pyrrolo[3,2-b]pyridine (10.7 mmol) in anhydrous DMF (15 mL) is added drop-wise to a stirred solution of NaH (60%, 160 mmol) in anhydrous DMF (25 mL) under N2 at 0° C. for 20 min and stirred at 0° C. under N2 for 30 minutes. HOSA (53.5 mmol) is added portion-wise for 30 minutes at 0° C., and stirred at 0° C. for 1.5 hours. After quenching with ice-water (400 mL), the mixture is extracted with ether (3×60 mL). The combined organic layer is washed with water (2×30 mL) and brine (20 mL), dried (Na2SO4), filtered, and concentrated in vacuo. The residue is purified by silica gel column chromatography eluting with 0-60% EtOAc in heptane to afford 5-fluoro-3-methyl-pyrrolo[3,2-b]pyridin-1-ylamine (570 mg). MS: 166 (M+H); 1H NMR (300 MHz, CDCl3) δ 2.32 (s, 3H), 4.82 (br, 2N—H), 6.76 (d, H), 7.17 (s, H), 7.77 (dd, H).