Sodium Carbonate → HCID 89908297, compound

Participants

Reaction Steps

3-Bromo-4-((3S,4S)-3,4-dihydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)benzamide (Stage 7.1, 60 mg, 0.13 mmol), pyrimidin-5-ylboronic acid (66.6 mg, 0.325 mmol), Pd(PPh3)2Cl2 (9.13 mg, 0.013 mmol) and Na2CO3 (68.9 mg, 0.650 mmol) were added to a MW vial. The vial was sealed, evacuated/purged with argon, and DME (552 μL), water (158 μL), EtOH (79 μL) were added. The RM was then subjected to MW irradiation at 120° C. for 10 min. The RM was diluted with DME (2 mL), treated with Si-Thiol (Silicycle, 1.27 mmol/g, 102 mg, 0.130 mmol), filtered and the filtrate was evaporated off under reduced pressure to give a residue which was purified by preparative HPLC (Condition 12, from 20% to 50% in 18 min) to yield the title compound as a white solid. UPLC-MS (condition 1) tR=2.10 min, m/z=461.0 [M+H]+, m/z=459.0 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 2.75 (d, J=10.27 Hz, 2H) 3.27 (dd, J=10.39, 3.55 Hz, 2H) 3.88 (br. s, 2H) 5.07 (d, J=3.42 Hz, 2H) 6.97 (d, J=8.80 Hz, 1H) 7.34 (d, J=8.31 Hz, 2H) 7.82-7.90 (m, 3H) 7.94 (dd, J=8.80, 2.45 Hz, 1H) 8.85 (s, 2H) 9.17 (s, 1H) 10.10 (s, 1H).

Provenance & Evidence