Sodium Carbonate → HCID 69087703, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl {1-[4-(2-bromo-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl)phenyl]cyclobutyl}carbamate (50.0 mg, 0.0895 mmol), N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]cyclopropanecarboxamide (38.6 mg, 0.134 mmol), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (6.34 mg, 0.00895 mmol) and 2 M Na2CO3 (0.0895 mL, 0.179 mmol) in DMF (1.00 mL) was heated at 160° C. under microwave irradiation for 1 hour. After cooling to room temperature, the mixture was diluted with water and extracted with CHCl3 (×3). The combined organic layers were dried over anhydrous Na2SO4 and concentrated. The residue was purified by PTLC (CHCl3/MeOH=9:1) to afford desired product (53.9 mg, 94.3%) as pale yellow solid. 1HNMR (CDCl3) 500 MHz δ: 8.15 (dd, J=7.7, 1.4 Hz, 1H), 8.02-7.97 (m, 1H), 7.70 (br s, 1H), 7.55-7.48 (m, 2H), 7.45-7.38 (m, 2H), 7.36-7.31 (m, 2H), 7.30-7.25 (m, 1H), 7.16-7.10 (m, 3H), 6.95 (d, J=8.0 Hz, 1H), 6.83-6.74 (m, 1H), 6.58 (dd, J=7.7, 4.9 Hz, 1H), 6.55-6.49 (m, 1H), 5.26 (br s, 1H), 2.59-2.24 (m, 4H), 2.19-2.06 (m, 1H), 1.95-1.79 (m, 1H), 1.57-1.19 (m, 10H), 1.09-1.02 (m, 2H), 0.84-0.75 (m, 2H).

Provenance & Evidence