反应详情

A solution of 3,3-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepine (0.43 g, 1.8 mmol) in DMF (20 mL) was cooled in an ice bath and treated drop-wise with Br2 (0.19 mL, 3.7 mmol). After stirring in the ice bath for 2.5 h, the reaction was quenched with H2O (25 mL) and NaHCO3 (50 mL) and extracted with EtOAc (3×100 mL). The combined organic layers were washed with H2O (2×50 mL) and brine (50 mL), dried over Na2SO4, filtered and concentrated to an orange oil. Purification by flash column chromatography (silica gel, CH2Cl2/MeOH, 98:2 to 96:4) gave the title compound (0.26 g, 54%) as a yellow solid: 1H NMR (300 MHz, DMSO-d6) δ 8.15 (d, J=2.3 Hz, 1H), 8.03 (s, 1H), 7.73 (d, J=2.3 Hz, 1H), 5.93 (br s, 1H), 3.09 (d, J=4.9 Hz, 2H), 1.30 (s, 6H); MS (ESI) m/e 254 (M+H)+.

1. customthe reaction was quenched with H2O (25 mL) and NaHCO3 (50 mL)
2. extractionextracted with EtOAc (3×100 mL)
3. washThe combined organic layers were washed with H2O (2×50 mL) and brine (50 mL)
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated to an orange oil
7. customPurification by flash column chromatography (silica gel, CH2Cl2/MeOH, 98:2 to 96:4)