Sodium Carbonate → HCID 69087699, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl {1-[4-(2-chloro-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl)phenyl]cyclobutyl}carbamate (50.0 mg, 0.0835 mmol), 4-methyl-3-nitrophenylboronic acid pinacol ester (33.6 mg, 0.125 mmol), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (5.91 mg, 0.00835 mmol) and 2M Na2CO3 aq. (0.0835 mL, 0.170 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 EtOAc and washed with water(×3). The organic layer was dried over anhydrous Na2SO4 and concentrated. The residue was purified by silica gel column chromatography (EtOAc/hexane=1:4→1:3→1:2) to afford desired product (49.1 mg, 95.7%) as pale yellow solid. 1HNMR (CDCl3) 400 MHz δ: 8.21 (s, 1H), 8.16 (dd, J=7.8, 1.4 Hz, 1H), 8.02 (dd, J=4.6, 1.4 Hz, 1H), 7.67 (dd, J=8.2, 1.8 Hz, 1H), 7.42 (d, J=8.2 Hz, 2H), 7.31 (td, J=7.6, 1.5 Hz, 1H), 7.22-7.11 (m, 4H), 7.00-6.93 (m, 1H), 6.85 (d, J=7.8 Hz, 1H), 6.61 (dd, J=7.8, 5.0 Hz, 1H), 6.50 (s, 1H), 5.24 (br s, 1H), 2.67-2.27 (m, 4H), 2.56 (s, 3H), 2.23-2.07 (m, 1H), 1.97-1.85 (m, 1H), 1.39 (br s, 9H).

Provenance & Evidence