Triisopropyl borate → HCID 57562462, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 5-methoxy-1H-pyrrolo[3,2-b]pyridine-1-carboxylate (3 g, 12.08 mmol) in 40 mL of dry THF was added dropwise t-BuLi (1.16 g, 18.12 mmol) at −78° C. Then the solution was stirred at −78° C. for 1 hour. Then triisopropyl borate (4.55 g, 24.17 mmol) was added dropwise to the solution still at −78° C. The mixture was stirred at −78° C. for 2 hours and quenched the reaction with 1 M of HCl at low temperature to pH=3˜4. After it was extracted with EtOAc, the combined organic phase was washed with brine, dried over Na2SO4. After concentrated, the resulting residue was purified using column (petroleum ether:ethyl acetate=3:1) to provide (1-(tert-butoxycarbonyl)-5-methoxy-1H-pyrrolo[3,2-b]pyridin-2-yl)boronic acid (1.3 g, yield: 37%). 1H-NMR (CDCl3, 400 MHz) δ 8.10 (d, J=9.2 Hz, 1H), 7.46 (s, 1H), 6.88˜6.84 (m, 2H), 6.70 (d, J=9.2 Hz, 1H), 3.98 (s, 3H), 1.71 (s, 9H). MS (M+H)+: 293.

Provenance & Evidence