Sodium hydride → HCID 67352869, compound

Participants

Reaction Steps

To a mixture of tert-butyl 1H-pyrrolo[3,2-c]pyridine-6-carboxylate (1.0 g, 4.6 mmol) in DMF (20 ml) was added sodium hydride (60% in oil) (0.4 g, 10 mmol) and stirred at room temperature for 3 h. To the mixture, (bromomethyl)cyclopropane (1.2 g, 9.2 mmol) was added and stirred at room temperature. for 2 h. The reaction mixture was extracted with EtOAc/H2O. The organic layer was washed with brine, dried over MgSO4 and concentrated in vacuo. The crude mixture was purified by chromatography (SiO2, hexanes:EtOAc=50:50) to give tert-butyl 1-(cyclopropylmethyl)-1H-pyrrolo[3,2-c]pyridine-6-carboxylate (2A, 1.1 g, 4.0 mmol, 88% yield) as a yellow oil. 1 H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.16-0.23 (m, 2 H) 0.44-0.51 (m, 2 H) 0.99-1.11 (m, 1H) 1.48 (s, 9 H) 3.84 (d, J=7.07 Hz, 2 H) 6.45-6.47 (m, 1 H) 7.19 (d, J=3.03 Hz, 1 H) 7.96 (s, 1 H) 8.79 (s, 1 H).

Provenance & Evidence