Triphenylphosphine → HCID 22507731, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 180 mg (0.40 mmol) (±)-2-bromo-N-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-isonicotinamide in 10 ml DMF were added 298 mg (0.80 mmol) tributyl-(3,6-dihydro-2H-pyran-4-yl)-stannane, 34 mg (0.05 mmol) bis(triphenylphosphine)palladium(II) chloride, 63 mg (0.24 mmol) triphenylphosphine, 136 mg (3.20 mmol) lithium chloride and a small spatula-end of 2,6-di-tert-butyl-4-methylphenol. The mixture was heated at 100° C. for 24 h and then concentrated in vacuo. Flash chromatography (ethyl acetate) afforded 140 mg (77%) (±)-2-(3,6-dihydro-2H-pyran-4-yl)-N-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-isonicotinamide as an off-white solid. ES-MS m/e (%): 454 (M+H+, 100).

Provenance & Evidence