Chloromethyl methyl sulfide → HCID 67356941, 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) (0.41 g, 10 mmol) and stirred at room temperature for 3 h. To the mixture, (chloromethyl)(methyl)sulfane (0.89 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-(methylthiomethyl)-1H-pyrrolo[3,2-c]pyridine-6-carboxylate (8A, 920 mg, 3.3 mmol, 72% yield) as a yellow oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.61 (s, 9H) 1.94 (s, 3H) 5.15 (s, 2H) 6.64 (d, J=3.28 Hz, 1H) 7.34 (d, J=3.28 Hz, 1H) 8.15 (s, 1H) 8.93 (d, J=1.01 Hz, 1H).

Provenance & Evidence