tert-Butanol → HCID 67353089, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of diphenylphosphoryl azide (1.7 g, 6.2 mmol), Et3N (2.9 ml, 21 mmol) and 1-(cyclopropylmethyl)-1H-pyrrolo[3,2-c]pyridine-6-carboxylic acid (2B, 0.9 g, 4.0 mmol) in 2-methylpropan-2-ol (10 g, 140 mmol) was stirred at room temperature for 1 h and 80° C. for 3 h. The mixture was extracted with EtOAct/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-(cyclopropylmethyl)-1H-pyrrolo[3,2-c]pyridin-6-ylcarbamate (2C, 300 mg, 25% 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