tert-Butanol → HCID 67357244, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of diphenylphosphoryl azide (4.3 g, 16 mmol), Et3N (7.3 ml, 52 mmol) and 3-bromo-1-ethyl-1H-pyrrolo[3,2-c]pyridine-6-carboxylic acid (3B, 2.8 g, 10 mmol) in DMF (30 ml) was stirred at 0° C. for 1 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 dissolved in toluene (30 ml) and added 2-methylpropan-2-ol (3.9 g, 52 mmol). The mixture was stirred at 70° C. for 2 h. The mixture was concentrated in vacuo and purified by chromatography (SiO2, hexanes:EtOAc=1:1) to give tert-butyl 3-bromo-1-ethyl-1H-pyrrolo[3,2-c]pyridin-6-ylcarbamate (3C, 340 mg, 0.99 mmol, 9.5% yield) as a white powder. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.35 (t, J=7.20 Hz, 3 H) 1.49 (s, 9 H) 4.14 (q, J=7.33 Hz, 2 H) 7.60 (s, 1 H) 7.83 (d, J=0.76 Hz, 1 H) 8.36 (d, J=0.76 Hz, 1 H) 9.59 (s, 1 H).

Provenance & Evidence