Dichloromethane → [5-[2-(4-Ethoxycarbonyl-4-methyl-1-piperidyl)pyrimidin-5-yl]-2-(3-ethyl-5-methyl-2-oxo-1,3,5-triazinan-1-yl)-1,3-benzothiazol-7-yl]boronic acid

Participants

Reaction Conditions

Reaction Steps

Ethyl 1-[5-[7-bromo-2-(3-ethyl-5-methyl-2-oxo-1,3,5-triazinan-1-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate (100 mg, 0.166 mmol), bis(neopentyl glycolato)diboron (75 mg, 0.33 mmol), Pd(dppf)Cl2.DCM (14 mg, 0.017 mmol), potassium acetate (49 mg, 0.50 mmol) and toluene (2 mL) were sealed in a microwave reaction vial under argon and heated at 130° C. for 40 min. The reaction mixture was diluted with n-hexane (10 mL) before being filtered to remove particulate palladium residues. The filtrate was concentrated to obtain desired product (118 mg, light brown solid). 1H NMR (MeOD) δ 8.63 (s, 2H), 7.91 (d, J=1.9 Hz, 1H), 7.82 (d, J=1.8 Hz, 1H), 5.20 (s, 2H), 4.44-4.34 (m, 4H), 4.21 (q, J=7.1 Hz, 2H), 3.50-3.42 (m, 2H), 3.33-3.28 (m, 2H, obscured by solvent), 2.65 (s, 3H), 2.21-2.13 (m, 2H), 1.69-1.38 (m, 2H), 1.33-1.19 (m, 9H). m/z [M+H]+ 568.1.

Provenance & Evidence