Sodium Carbonate → HCID 69087689, 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), 1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]piperidin-2-one (40.5 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, EtOAc/CHCl3=1:1) to afford desired product (31.9 mg, 54.6%) as a pale yellow solid. 1HNMR (CDCl3) 500 MHz δ: 8.16 (dd, J=7.7, 1.4 Hz, 1H), 8.03-7.97 (m, 1H), 7.61 (d, J=8.0 Hz, 2H), 7.35 (d, J=8.0 Hz, 2H), 7.31-7.25 (m, 1H), 7.21-7.10 (m, 5H), 6.95 (d, J=7.4 Hz, 1H), 6.84-6.69 (m, 1H), 6.59 (dd, J=8.0, 4.6 Hz, 1H), 6.51-6.45 (m, 1H), 5.21 (br s, 1H), 3.64-3.57 (m, 2H), 2.61-2.26 (m, 6H), 2.18-2.07 (m, 1H), 1.97-1.80 (m, 5H), 1.40 (br s, 9H).

Provenance & Evidence