Pyridine → HCID 67355294, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl 1-(methylsulfonylmethyl)-1H-pyrrolo[3,2-c]pyridin-6-ylcarbamate (8D, 420 mg, 1.3 mmol) in 4M HCl in dioxane (3 ml) was stirred at 50° C. for 3 h. The mixture was concentrated in vacuo and the resulting residue was dissolved in pyridine (3 ml, 37.1 mmol). To the mixture, methyl 4-(chlorocarbonyl)benzoate (385 mg, 1.936 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 (NH—SiO2, EtOAc) to give methyl 4-(1-(methylsulfonylmethyl)-1H-pyrrolo[3,2-c]pyridin-6-ylcarbamoyl)benzoate (8E, 160 mg, 0.40 mmol, 31% yield) as a white powder. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.02 (s, 3H) 3.90 (s, 3H) 5.88 (s, 2H) 6.73 (d, J=2.78 Hz, 1H) 7.49 (d, J=3.28 Hz, 1H) 8.01-8.12 (m, 2H) 8.12-8.19 (m, 2H) 8.46 (s, 1H) 8.70 (s, 1H) 10.93 (s, 1H).

Provenance & Evidence