Sodium Bicarbonate → HCID 69087722, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl {1-[4-(2-chloro-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl)phenyl]cyclobutyl}carbamate (50 mg, 0.097 mmol) in DMF (1 mL) was added saturated NaHCO3, 4-benzyloxyphenylboronic acid (45 mg, 0.20 mmol) and PdCl2(Me2NPhP(tBu)2)2 (7 mg, 0.0097 mmol). The reaction was degassed for 2 minutes and then heated at 160° C., 1 h (microwave reactor). The reaction mixture was cooled to room temperature, then was diluted with EtOAc (15 mL) and washed with brine. The organic phase was dried over sodium sulfate, filtered and concentrated. Purification by column chromatography (SiO2, 10% to 50% EtOAc in hexane) gave the title compound as a yellow solid (56 mg). 1HNMR (CDCl3) 400 MHz δ: 8.17-8.15 (m, 1H), 8.00-7.99 (m, 1H), 7.51 (d, J=8.6 Hz, 2H), 7.48-7.23 (m, 8H), 7.15-7.13 (m, 3H), 6.94 (d, J=7.4 Hz, 1H), 6.89 (d, J=8.6 Hz, 2H), 6.79 (d, J=7.4 Hz, 1H), 6.59 (dd, J=7.7, 4.9 Hz, 1H), 6.30 (s, 1H), 5.12 (br s, 1H), 5.05 (s, 2H), 2.53-2.51 (m, 4H), 2.15-2.12 (m, 1H), 1.93-1.84 (m, 1H), 1.39 (br s, 9H).

Provenance & Evidence