Sodium Carbonate → HCID 89907395, compound

Participants

Reaction Steps

(R)-6-(3-Hydroxypyrrolidin-1-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 9.1, 60 mg, 0.122 mmol), 5-bromothiazole (29.9 mg, 0.182 mmol), PdCl2(dppf)-(CH2Cl2) (9.93 mg, 0.012 mmol), Na2CO3 (38.7 mg, 0.365 mmol) DME (627 μL) and water (111 μL) were added to a MW vial, which was sealed, evacuated/purged with argon and was subjected to MW irradiation at 125° C. for 10 min. Additional 5-bromothiazole, (29.9 mg, 0.182 mmol) was added MW irradiation was continued at 125° C. for 10 min. The RM was stirred with Si-Thiol (1.27 mmol/g, 47.9 mg, 0.061 mmol), filtered and the filtrate was evaporated off under reduced pressure to give a residue which was purified by preparative HPLC (Condition 9, 25% for 0.2 min then 25% to 55% in 14 min) to afford the title compound as a white solid. UPLC-MS (Condition 1) tR=2.17 min, m/z=451.0-452.0 [M+H]+, m/z=449.0-450.0 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.70-1.79 (m, 1H) 1.80-1.91 (m, 1H) 3.00 (d, J=11.49 Hz, 1H) 3.25-3.31 (m, 2H) 3.42-3.51 (m, 1H) 4.19-4.25 (m, 1H) 4.74-4.99 (m, 1H) 7.34 (d, J=8.56 Hz, 2H) 7.82-7.88 (m, 2H) 7.91 (s, 1H) 8.08 (d, J=2.45 Hz, 1H) 8.78 (d, J=2.45 Hz, 1H) 9.19 (s, 1H), 10.19 (s, 1H).

Provenance & Evidence