Dichloromethane → HCID 86696350, compound

Participants

Reaction Steps

(3-{[3-(5-Acetyl-thiophen-2-yl)-imidazo[1,2-b]pyridazin-6-yl]-methyl-amino}-propyl)-carbamic acid tert-butyl ester was prepared and isolated similarly to the procedure detailed in example 5.6.17 from a mixture of {3-[(3-bromo-imidazo[1,2-b]pyridazin-6-yl)-methyl-amino]-propyl}-carbamic acid tert-butyl ester (0.5 g, 1.3 mmol), 5-acetyl-2-thiopheneboronic acid [206551-43-1] (0.3 g, 1.5 mmol), potassium phosphate tribasic monohydrate [27176-10-9] (0.5 g, 2.5 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane [95464-05-4] (0.1 g, 0.1 mmol) in a solution of 30% (v/v) water in 1,2-dimethoxyethane (30 mL) to afford 0.16 g of yellow powder, mp. 148-149° C. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.37 (s, 9H) 1.78 (quin, J=6.95 Hz, 2H) 2.54 (s, 3H) 3.05 (q, J=6.57 Hz, 2H) 3.17 (s, 3H) 3.61 (t, J=7.20 Hz, 2H) 6.88 (br. s., 1H) 7.12 (d, J=9.85 Hz, 1H) 7.82 (d, J=4.29 Hz, 1H) 7.92 (d, J=9.85 Hz, 1H) 7.97 (d, J=4.04 Hz, 1H) 8.20 (s, 1H). LRMS (ESI) m/z 430.1 [(M+H)]+, calc'd for C21H27BN5O3S: 429.55.

Provenance & Evidence