Sodium Carbonate → HCID 69087722, compound

Participants

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 (400 mg, 0.778 mmol), [4-(benzyloxy)phenyl]boronic acid (355 mg, 1.56 mmol), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (55 mg, 0.078 mmol), and 2M Na2CO3 aq. (0.780 mL, 1.56 mmol) in DMF (8 mL) was treated with microwave (160° C. for 1 hour). The mixture was diluted with AcOEt, washed with water(×3), brine, dried over Na2SO4, then filtrated through Celite pad. The filtrate was concentrated and the residue was purified by column chromatography (n-hexane/AcOEt=3:2) to afford the mixture of the desired product (430 mg, 84%) as a pale yellow solid. 1HNMR (CDCl3) 400 MHz δ: 8.16 (dd, J=8.0, 1.1 Hz, 1H), 8.00 (d, J=4.0 Hz, 1H), 7.51 (d, J=8.0 Hz, 2H), 7.43 (d, J=8.0 Hz, 2H), 7.39-7.33 (m, 4H), 7.32-7.28 (m, 2H), 7.16-7.12 (m, 3H), 6.94 (d, J=8.0 Hz, 1H), 6.89 (d, J=8.6 Hz, 2H), 6.79 (d, J=7.4 Hz, 1H), 6.59 (dd, J=8.0, 4.6 Hz, 1H), 6.26 (s, 1H), 5.10 (br s, 1H), 5.05 (s, 2H), 2.56-2.46 (m, 4H), 2.18-2.09 (m, 1H), 1.93-1.84 (m, 1H), 1.39 (br s, 9H). LCMS: 662 [M+H].

Provenance & Evidence