Sodium Carbonate → HCID 68067477, 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 (250 mg, 0.486 mmol), 4-nitrophenylboronic acid pinacol ester (152 mg, 0.730 mmol), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (34.4 mg, 0.0486 mmol) and 2M Na2CO3 aq. (0.485 mL, 0.970 mmol) in DMF (1.00 mL) was heated at 160° C. under microwave irradiation for 1 hour under nitrogen. 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→1:2) and TLC (EtOAc/hexane=1:1, DCM/EtOAc=1:1) to afford desired product (51.4 mg, 17.6%) as yellow solid. 1HNMR (CDCl3) 400 MHz δ: 8.19-8.08 (m, 3H), 8.06-8.01 (m, 1H), 7.80-7.70 (m, 2H), 7.47-7.40 (m, 2H), 7.36-7.30 (m, 1H), 7.22-7.14 (m, 3H), 7.00-6.93 (m, 1H), 6.85-6.78 (m, 1H), 6.65-6.58 (m, 1H), 6.38 (s, 1H), 5.19 (s, 1H), 2.67-2.30 (m, 4H), 2.25-2.09 (m, 1H), 1.98-1.84 (m, 1H), 1.39 (br s, 9H).

Provenance & Evidence