Sodium Carbonate → HCID 131735902, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of N-[3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-4-(trifluoromethyl)pyrimidin-2-amine (2.00 g, 5.27 mmol), 3,5-dibromopyridine (4.37 g, 18.5 mmol) and Pd(dppf)Cl2—CH2Cl2 (0.215 g, 0.264 mmol) in 1,4-dioxane (26.4 mL, 0.2 M), and Na2CO3 (5.27 mL, 2.00 M) was purged with argon and heated to 80° C. for 4 hours. The reaction mixture was filtered through a CELITE plug and washed with dichloromethane. The eluent was diluted with water and extracted with dichloromethane (3×). The combined organic layers were concentrated in vacuo and the residue was purified by silica gel chromatography (ethyl acetate/hexanes) to afford N-[3-(5-bromopyridin-3-yl)-5-methylphenyl]-4-(trifluoromethyl)pyrimidin-2-amine. MS APCI calc'd for C17H13BrF3N4 [M+H]+ 409 and 411. found 409 and 411.

Provenance & Evidence