tert-Butanol → HCID 67355878, compound

Participants

Reaction Steps

A mixture of diphenylphosphoryl azide (1.1 g, 3.8 mmol), Et3N (1.8 ml, 13 mmol) and 1-(methylsulfonylmethyl)-1H-pyrrolo[3,2-c]pyridine-6-carboxylic acid (8C, 650 mg, 2.6 mmol) in 2-methylpropan-2-ol (10 g, 140 mmol) was stirred at room temperature for 1 h and then at 80° C. 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 (SiO2, hexane:EtOAc=50:50) to give tert-butyl 1-(methylsulfonylmethyl)-1H-pyrrolo[3,2-c]pyridin-6-ylcarbamate (8D, 410 mg, 1.3 mmol, 50% yield) as a white powder. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.35-0.44 (m, 2H) 0.57-0.70 (m, 2H) 1.19-1.33 (m, 1H) 1.57 (s, 9H) 3.97 (d, J=6.82 Hz, 2H) 6.52-6.54 (m, 1H) 7.19 (d, J=3.28 Hz, 1H) 7.59 (br. s., 1H) 7.93 (s, 1H) 8.56 (d, J=1.01 Hz, 1H).

Provenance & Evidence