3-Amino-5-bromopyridine → HCID 131735903, 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 (4.00 g, 10.6 mmol), 5-bromopyridin-3-amine (2.01 g, 11.6 mmol), Pd(dppf)Cl2—CH2Cl2 (0.431 g, 0.527 mmol) in 1,4-dioxane (52.7 mL, 0.2 M) and Na2CO3 (10.6 mL, 2 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 purified by silica gel column chromatography (methanol/ethyl acetate) to afford N-[3-(5-aminopyridin-3-yl)-5-methylphenyl]-4-(trifluoromethyl)pyrimidin-2-amine. MS APCI calc'd for C17H15F3N5 [M+H]+ 346. found 346.

Provenance & Evidence