Potassium Carbonate → HCID 58169313, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(2-bromo-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidin-5-yl)ethyl acetate (366 mg, 1.0 mmol, 1.0 eq), N-tert-butyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-sulfonamide (517 mg, 1.5 mmol, 1.5 eq), PdCl2(dppf) (81.6 mg, 0.1 mmol, 0.1 eq), K2CO3 (417 mg, 3.0 mmol, 3.0 eq), dioxane (15 mL) and water (2 mL) was heated for 1 h at 90° C. under nitrogen atmosphere. The solvent was removed and the residue was purified by silica gel chromatography (PE/EtOAc=1:1) to yield 2-(2-(5-(N-tert-butylsulfamoyl)thiophen-2-yl)-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidin-5-yl)ethyl acetate (300 mg, 60%). LC-MS (m/z)=505.1 [M+H]+; 1H NMR (400 MHz, DMSO-d6): δ 0.73-0.74 (m, 2H), 0.96-0.97 (m, 2H), 1.16 (s, 9H), 1.90-1.94 (m, 1H), 1.97 (s, 3H), 2.96 (t, J=5.6 Hz, 2H), 4.17 (d, J=5.6 Hz, 2H), 6.47 (s, 1H), 7.58 (d, J=4.0 Hz, 1H), 7.72 (d, J=4.0 Hz, 1H), 7.87 (s, 1H), 8.13 (s, 1H), 9.37 (s, 1H), 12.19 (s, 1H)

Provenance & Evidence