Methyl 4-(chlorocarbonyl)benzoate → HCID 67356193, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl 3-bromo-1-ethyl-1H-pyrrolo[3,2-c]pyridin-6-ylcarbamate (3C, 340 mg, 0.99 mmol) in 4M HCl in dioxane (3 ml) was stirred at room temperature for 1 h and 70° C. for 2 h. The mixture was concentrated in vacuo and dissolved in pyridine (3 ml). To the mixture, methyl 4-(chlorocarbonyl)benzoate (220 mg, 1.1 mmol) was added and stirred at room temperature for 3 h. The 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 (basic-SiO2, hexanes:EtOAc=3:1) to give methyl 4-(3-bromo-1-ethyl-1 H-pyrrolo[3,2-c]pyridin-6-ylcarbamoyl)benzoate (3D, 350 mg, 0.87 mmol, 87% yield) as a white powder. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.40 (t, J=1.00 Hz, 3 H) 3.90 (s, 3 H) 4.21 (q, J=7.16 Hz, 2H) 7.72 (s, 1 H) 7.99-8.11 (m, 2 H) 8.11-8.20 (m, 2 H) 8.35 (d, J=0.76 Hz, 1 H) 8.52 (d, J=1.01 Hz, 1 H) 10.96 (s, 1 H).

Provenance & Evidence