Cesium carbonate → HCID 68810783, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 6-chloro-2-(2-(7-methoxyquinolin-4-yloxy)ethyl)pyridazin-3(2H)-one (255 mg, 769 μmol), (R)—N—((S)-1-(2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2,2,2-trifluoroethyl)-2-methylpropane-2-sulfinamide (260 mg, 591 μmol), dichloro[1,1′bis(diphenylphoshino)ferrocene]palladium(II) dichloromethane adduct (43.3 mg, 59.1 μmol), cesium carbonate (771 mg, 2365 μmol) in 1,4-dioxane (3 mL) and water (0.75 mL) was sparged with argon for 5 minutes then heated to 90° C. with stirring for 2 hours The reaction was then partitioned between 9:1 CHCl3/IPA (25 mL) and 5% NaHCO3 (10 mL). The organic layer was then dried over MgSO4, concentrated, then purified on silica (40 g) eluting with 2 to 3% MeOH/DCM. Product was isolated as an off white solid from ACN. MS (ESI pos. ion) m/z: 609 (MH+); calc'd for C28H28ClF3N4O4S: 608. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.27 (s, 9 H) 3.87 (d, J=8.02 Hz, 1 H) 3.91 (s, 3 H) 4.66 (t, J=5.38 Hz, 2 H) 4.80 (t, J=5.28 Hz, 2 H) 5.46-5.56 (m, 1 H) 6.68 (d, J=5.28 Hz, 1 H) 7.00-7.09 (m, 2 H) 7.34 (d, J=2.35 Hz, 1 H) 7.52 (d, J=8.22 Hz, 1 H) 7.59-7.66 (m, 2 H) 7.84 (d, J=1.96 Hz, 1 H) 7.99 (d, J=9.19 Hz, 1 H) 8.64 (d, J=5.28 Hz, 1 H). 19F NMR (377 MHz, CHLOROFORM-d) δ ppm −73.59 (d, J=8.01 Hz, 3 F).

Provenance & Evidence