Potassium Phosphate, Tribasic → HCID 66730797, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (S)-N-allyl-6-(3-cyano-6-cyclopropyl-1H-indol-2-yl)-N-(1,1,1-trifluoropropan-2-yl)pyridine-3-sulfonamide (140 mg, 0.30 mmol), 2-bromo-pyrimidine (98 mg, 0.59 mmol), copper (I) iodide (11 mg, 0.06 mmol), (1R,2R)-N1,N2-dimethylcyclohexane-1,2-diamine (0.02 mL, 0.12 mmol), and K3PO4 (134 mg, 0.60 mmol) in toluene was stirred at 100° C. for 16 hrs. The mixture was then filtered through celite and the solvent evaporated. The residue was purified on silica gel eluting with 0 to 10% ethyl acetate in CH2Cl2 to provide (S)-N-allyl-6-(3-cyano-6-cyclopropyl-1-(pyrimidin-2-yl)-1H-indol-2-yl)-N-(1,1,1-trifluoropropan-2-yl)pyridine-3-sulfonamide (140 mg, 86%). MS m/z 553.3 M+H+; 1H NMR (500 MHz, CDCl3): δ 8.65 (1H, d, J=3.0 Hz), 8.62 (2H, d, J=4.0 Hz), 8.14 (1H, dd, J=4.0, 8.0 Hz), 8.01 (1H, d, J=9.0 Hz), 7.75 (1H, s), 7.64 (1H, d, J=7.5 Hz), 7.21-7.19 (1H, m), 7.04 (1H, d, J=9.0 Hz), 5.60 (1H, m), 5.28-5.25 (2H, m), 4.50 (1H, m), 3.86 (1H, d, J=6.5 Hz), 2.02-1.96 (1H, m), 1.32 (3H, d, J=8.5 Hz), 0.98-0.96 (2H, m), 0.75-0.72 (2H, m).

Provenance & Evidence