Benzene → Isopropyl 6-bromo-2-(oxazol-5-yl)-1H-pyrrolo[3,2-c]pyridine-1-carboxylate

Participants

Reaction Steps

5-(6-Bromo-1H-pyrrolo[3,2-c]pyridin-2-yl)oxazole (Preparation 139, 156 mg 0.59 mmole) was azeotroped with benzene (3 mL) and then dissolved in DMF (1.5 mL). The solution was placed under nitrogen and a solution of sodium hexamethyldisilazide (1M in THF, 0.9 mL, 0.9 mmole) was added and stirred at room temperature for 20 minutes. A solution of isopropyl chloroformate (1M in toluene, 0.9 mL, 0.9 mmole) was added and stirred at room temperature for 4 hours. The reaction was diluted with ethyl acetate (25 mL) and the solution was washed with water (3×10 mL), brine, dried and evaporated to a residue. This was purified using preparative TLC eluting with 3:1 ethyl acetate:cyclohexane. The product band was recovered with acetone to afford the title compound (154 mg, 74%). 1H-NMR (CDCl3, 500 MHz): δ 1.36 (d, J=6.31 Hz, 6H), 5.23 (sept, J=6.31 Hz, 1H), 6.94 (d, J=0.63 Hz, 1H), 7.41 (s, 1H), 8.02 (s, 1H), 8.32 (t, J=0.95 Hz, 1H), 8.69 (d, J=0.95 Hz, 1H).

Provenance & Evidence