反应详情

Methyl-[2-(3-phenyl-imidazo[1,2-b]pyridazin-6-ylamino)-ethyl]-carbamic acid tert-butyl ester was prepared similarly to the procedure for example 5.6.60 from [2-(3-bromo-imidazo[1,2-b]pyridazin-6-ylamino)-ethyl]-methyl-carbamic acid tert-butyl ester (370.3 mg, 1.0 mmol), phenylboronic acid [98-80-6] (146.4 mg, 1.2 mmol), potassium phosphate tribasic monohydrate [27176-10-9] (460.2 mg, 2.0 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane [95464-05-4] (81.9 mg, 0.1 mmol) in 30% (v/v) water in 1,2-dimethoxyethane (12.5 mL) at 85° C. for 17 h. Off white powder from ethyl acetate/heptane, mp. 150-151° C. 1H NMR (400 MHz, DMSO-d6) δ ppm (rotamers present) 1.16 (br. s., 5H) 1.20-1.33 (m, 1H) 1.37 (br. s., 3H) 2.49-2.54 (m, 1H) 2.83 (br. s., 3H) 3.43 (br. s., 2H) 3.51 (br. s., 1H) 6.69 (d, J=8.84 Hz, 1H) 7.22 (br. s., 1H) 7.29-7.38 (m, 1H) 7.43-7.54 (m, 2H) 7.76 (d, J=8.84 Hz, 1H) 7.89 (br. s., 1H) 8.16 (d, J=6.82 Hz, 2H). 13C NMR (100 MHz, DMSO-d6) δ ppm 14.39, 22.55, 28.24, 28.49, 31.71, 34.17, 35.10, 46.33, 47.00, 78.60, 112.58, 126.28, 127.46, 128.93, 130.40, 134.52, 153.69, 155.40. LRMS (ESI) m/z 368.1 [(M+H)]+, calc'd for C20H25N5O2: 367.45.