2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl → HCID 67318159, compound

Participants

Reaction Conditions

Reaction Steps

A pyrex reaction tube was charged with tris(dibenzylideneacetone)dipalladium (20 mg, 0.021 mmol), 4-(7-methoxy-1,5-naphthyridin-4-ylthio)benzenamine (122 mg, 0.430 mmol), sodium tert-butoxide (99 mg, 1.031 mmol), S-Phos (35 mg, 0.086 mmol), and 3-chloro-4-ethyl-6-p-tolylpyridazine (100 mg, 0.430 mmol). The reaction tube was purged with nitrogen. 1.3 mL of toluene was added, and the tube was sealed. The reaction mixture was heated at 100° C. for 3 h. Upon cooling, the mixture was diluted with 5% iPrOH/EtOAc and washed with water. The organic portion was dried with MgSO4, filtered and concentrated. The crude material was purified by silica gel chromatography (90/10/1 CH2Cl2/MeOH/NH4OH) and reverse phase chromatography (Gilson, 10-95% CH3CN over 15 min) to provide 4-ethyl-N-(4-(7-methoxy-1,5-naphthyridin-4-ylthio)phenyl)-6-p-tolylpyridazin-3-amine as a light yellow solid. MS m/z=480 [M+H]+. Calc'd for C28H25N5OS: 479.60.

Provenance & Evidence