2-Bromopropane → 2-amino-9-isopropyl-9H-pyrido[2,3-b]indole-3-carboxamide

To a solution of 2-amino-9H-pyrido[2,3-b]indole-3-carboxamide (5, 122 mg, 0.540 mmol) in DMF (5 mL) was added NaH (110 mg, 2.75 mmol) and the reaction was stirred for 10 min. 2-Bromopropane (111 μL, 0.688 mmol) was added and the mixture was stirred at RT for another 2.5 h. The reaction was quenched with water (50 mL), poured into a separatory funnel containing EtOAc (150 mL), the mixture was shaken and the layers were separated. The organic layer was washed with brine (100 mL), dried, filtered and concentrated. The crude product was purified by silica gel chromatography (MeOH/CH2Cl2 gradient) to yield 2-amino-9-isopropyl-9H-pyrido[2,3-b]indole-3-carboxamide as a white powder (13, 30 mg, 21%). NH4OAc standard conditions. DAD Retention time=6.95 min. M+H=269. 1H NMR (300 MHz, DMSO-d6): 8.72 (s, 1H), 7.82 (d, J=7.8 Hz, 1H), 7.61 (d, J=8.1 Hz, 1H), 7.54 (br s, 2H), 7.29 (ddd, J=8.4, 8.4, 1.2 Hz, 1H), 7.17 (ddd, J=7.5, 7.5, 0.9 Hz, 1H), 5.23 (septet, J=6.9 Hz, 1H), 1.60 (d, J=6.9 Hz, 6H).

1. stirringthe mixture was stirred at RT for another 2.5 h
2. customThe reaction was quenched with water (50 mL)
3. additionpoured into a separatory funnel
4. additioncontaining EtOAc (150 mL)
5. stirringthe mixture was shaken
6. customthe layers were separated
7. washThe organic layer was washed with brine (100 mL)
8. customdried
9. filtrationfiltered
10. concentrationconcentrated
11. customThe crude product was purified by silica gel chromatography (MeOH/CH2Cl2 gradient)

ORD record

ord-321885a55cd8484e86cdd6de87ce5d3e

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08101604B2