Cesium carbonate → HCID 86664010, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-allyl-1-(5-(7-bromo-2-(3-ethylureido)benzothiazol-5-yl)pyrimidin-2-yl)piperidine-4-carboxylate (0.45 g, 0.78 mmol) in DMSO (5.0 mL) was added bis(neopentylglycolato)diboron (0.35 g, 1.57 mmol) and potassium acetate (0.11 g, 1.17 mmol) and the mixture degassed by purging N2 for 15 min followed by addition of dichloro(1,1-bis(diphenylphosphino)ferrocene)palladium (II) (0.057 g, 0.078 mmol). The reaction mixture was again degassed for 10-15 min then heated up to 80° C. for 2 h. After reaction completion the mixture was cooled to rt followed by the addition of 2-chloropyrazine (0.20 g, 1.17 mmol) and aqueous solution of Cs2CO3 (0.38 g, 1.17 mmol, dissolved in minimum amount of water) and the mixture degassed by purging N2 for 15 min followed by addition of tetrakis(triphenylphosphine)palladium (0) (0.09 g, 0.078 mmol). The reaction mixture was again degassed for 10-15 min then heated up to 80° C. for 16 h. After reaction completion, the mixture was poured into 100 mL of ice-cold water, extracted with EtOAc (3×150 mL) and the combined organic layer washed with brine, dried over Na2SO4, filtered and evaporated. The crude residue was purified over 100-200 M silica-gel using 1.50% MeOH: DCM to obtain the desired product as a beige solid (0.26 g, 58% yield). 1H NMR (DMSO-d6): δ 1.09 (t, J=7.20 Hz, 3H), 1.21 (t, J=6.80 Hz, 3H), 1.47 (m, 2H), 2.05 (m, 2H), 2.29 (m, 2H), 3.18 (m, 2H), 3.21 (q, J=7.20, 2H), 4.17 (q, J=6.80 Hz, 2H), 4.46 (m, 2H), 5.05 (m, 2H), 5.72 (m, 1H) 6.80 (br s, 1H), 8.04 (s, 1H), 8.40 (s, 1H); 8.69 (s, 1H), 8.87 (s, 1H), 8.94 (s, 2H), 9.77 (s, 1H) and 10.64 (br s, 1H).

Provenance & Evidence