Potassium Phosphate, Tribasic → HCID 67104624, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-bromo-4-(2-fluoro-4-methylphenylamino)-7-methoxycinnoline-3-carboxamide hydrochloride (Example 54, 1.40 g, 3.169 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (1.47 g, 4.75 mmol), tripotassium phosphate (2.018 g, 9.51 mmol), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (0.260 g, 0.63 mmol) and tris(dibenzylideneacetone)dipalladium(0) (0.29 g, 0.32 mmol) in n-butanol (4.53 ml) and water (1.81 ml) was stirred under N2 (g) at 100° C. overnight. The reaction mixture was cooled, concentrated under reduced pressure and the residue purified with silica chromatography (CH2Cl2/MeOH) to give 1.54 g (96%) of a light brown solid. 1H NMR: 11.54 (s, 1H), 8.79 (s, 1H), 7.94 (s, 1H), 7.62 (s, 1H), 7.25 (m, 2H), 7.08 (m, 2H), 5.56 (s, 1H), 3.97 (s, 3H), 3.82 (m, 2H), 3.37 (m, 2H), 2.35 (s, 3H), 2.14 (m, 2H), 1.41 (s, 6H), 1.06 (s, 9H); m/z 508.

Provenance & Evidence