Potassium Phosphate, Tribasic → HCID 89907205, compound

Participants

Reaction Conditions

Reaction Steps

(R)-5-Bromo-N-(4-(chlorodifluoromethoxy)phenyl)-6-(3-hydroxypyrrolidin-1-yl)nicotinamide (Stage 171.1, 150 mg, 0.324 mmol), 2,4-dimethoxypyrimidin-5-ylboronic acid (71.6 mg, 0.389 mmol), PdCl2(dppf)-(CH2Cl2) (39.7 mg, 0.049 mmol) and K3PO4 (206 mg, 0.973 mmol) were added to a vial and flushed with argon. Dioxane (1.5 mL) was added and the mixture was stirred at 120° C. overnight. The solvent was evaporated off under reduced pressure, the residue was treated with Si-Thiol (Biotage, load: 1.3 mmol/g) in MeOH and purified by preparative SFC (Column DEAP, from 18% to 23% in 6 min) to afford the title compound as an off-white powder after lyophilization from water/MeCN. UPLC-MS (Condition 11), tR=1.05 min, m/z=522.3/524.2 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.66-1.92 (m, 2H) 2.89-3.43 (m, 4H) 3.91 (br. s, 3H) 3.95 (s, 3H) 4.21 (br. s, 1H) 4.74-5.00 (m, 1H) 7.33 (d, J=8.91 Hz, 2H) 7.83-7.90 (m, 3H) 8.32 (br. s, 1H) 8.74 (d, J=2.26 Hz, 1H) 10.11 (s, 1H).

Provenance & Evidence