2-Amino-4-methylpyridine → (4-Methyl-pyridin-2-yl)-[6-(2-pyridin-3-yl-thiazol-5-yl)-pyridin-2-yl]-amine

Participants

Reaction Conditions

Reaction Steps

A sealed tube was charged with 2-bromo-6-(2-pyridin-3-yl-thiazol-5-yl)-pyridine (125 mg, 0.392 mmol), 2-amino-4-methylpyridine (51 mg, 0.471 mmol), Pd(OAc)2 (1.8 mg, 8.01 μmol), BINAP (7.4 mg, 11.9 μmol), Cs2CO3 (255 mg, 0.782 mmol), and anhydrous and degassed toluene (2 ml) and heated to 110° C. with stirring for 48 h. The cooled reaction mixture was treated with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4, filtered and evaporated under reduced pressure before purification by column chromatography on SiO2 using combiflash Companion®, eluting with cyclohexane/ethyl acetate 100/0 to 0/100. The solid obtained was then triturated in methanol, filtered and dried to afford the title compound as a yellow solid. 1H NMR (DMSO-d6, 300 MHz): δ=9.74 (s, 1H), 9.15 (d, J=2.1 Hz, 1H), 8.68 (m, 1H), 8.59 (s, 1H), 8.31 (m, 1H), 8.10 (d, J=5.1 Hz, 1H), 7.93 (s, 1H), 7.72 (dd, J=8.2-7.6 Hz, 1H), 7.66-4.40 (m, 3H), 6.77 (d, J=4.9 Hz, 1H), 2.37 (s, 3H). (APCI+) m/z 346 (M+H)+.

Provenance & Evidence