Ammonia → Ethyl 1h-pyrrolo[3,2-c]pyridin4-ylcarbamate

Participants

Reaction Conditions

Reaction Steps

Sodium metal (0.067 g, 2.9 mmol, 10 eq) was added to a solution of ethyl 1-benzyl-1H-pyrrolo[3,2-c]pyridin-4-ylcarbamate (0.086 g, 0.29 mmol, 1.0 eq) in a mixture of liquid NH3 (5 mL) and THF (1 mL) at −78° C. The dark blue reaction mixture was stirred at −78° C. for 5 minutes and then was quenched with solid NH4Cl. The clear solution was allowed to warm to room temperature, treated with 10% NaHCO3 and extracted with 10/1 CHCl3/MeOH. The combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo to afford the product (0.059 g, 100%) as a solid. 1H NMR (CD3OD) δ 7.74 (d, 1H, J=6.0 Hz), 7.21 (d, 1H, J=3.4 Hz), 7.09 (d, 1H, J=5.7Hz), 6.59 (d, 1H, J=3.4Hz), 4.15 (q, 2H, J=7.1 Hz), 1.25 (t, 3H, J=7.1 Hz); MS(ESI+) m/z 206 (M+H)+. Calculated: 206.0930, found: 206.0932.

Provenance & Evidence