Methanol → Ethyl 1-(5-(7-bromo-2-(3-ethylureido)benzo[d]thiazol-5-yl)pyrimidin-2-yl)-4-methylpiperidine-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(7-bromo-5-iodobenzo[d]thiazol-2-yl)-3-ethylurea (22.7 g, 53.20 mmol) and ethyl 4-methyl-1-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl)piperidine-4-carboxylate (20 g, 53.2 mmol) in 1,4-dioxane:MeOH (300:180 mL) was added potassium phosphate (17 g, 79 mmol) at rt. The resulting mixture was degassed for 15-20 min by purging N2 followed by addition of tetrakis(triphenylphosphine)palladium(0) (6.1 g, 5.32 mmol). The reaction mixture was again degassed for another 15-20 min then heated up to 80° C. or 5 h. After completion of reaction (by TLC), the reaction was cooled to rt, diluted with EtOAc (500 mL) and passed through celite. The filtrate was evaporated and the crude residue purified over 100-200 M silica-gel by using 1.50% MeOH: DCM to obtain the desired product as an off-white solid (12 g, 41%). 1H NMR (DMSO-d6): δ 1.09 (t, J=7.20 Hz, 3H), 1.20 (m, 6H), 1.45 (m, 2H), 2.03 (m, 2H), 3.16 (m, 2H), 3.30 (q, J=7.20, 2H), 4.12 (q, J=6.80 Hz, 2H), 4.25 (m, 2H), 6.75 (br s, 1H), 7.69 (s, 1H), 7.86 (s, 1H); 8.75 (s, 2H) and 10.91 (br s, 1H). MS: 547.11 [M+H]+.

Provenance & Evidence