Dichloromethane → HCID 58529316, compound

Participants

Reaction Conditions

Reaction Steps

3-(4-Amino-5-bromopyrrolo[2,1-f][1,2,4]triazin-7-yl)-propan-1-ol (4.0 g, 14.75 mmol) and 2-benzyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2H-indazole (6.66 g, 19.9 mmol, 1.35 eq) were dissolved in 1:1 v/v EtOH-toluene and degassed with nitrogen. After 30 minutes [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane (1.20 g, 1.47 mmol, 0.1 eq) followed by 2M sodium carbonate solution (22 mL, 44.26 mmol, 3.0 eq) were added. The reaction mixture was stirred at 80° C. for 6 h. The reaction mixture was partitioned between EtOAc and water and filtered through a pad of Celite® to rid of excess palladium salts. The organic layer was washed with water and brine, dried over Na2SO4, filtered, and concentrated at reduced pressure. The crude product was purified by MPLC eluted with 10% MeOH/DCM with 1% Et3N to give the desired product as white foam (3.41 g, 58%). 1H-NMR (DMSO-d6) 8.53 (s, 1H), 7.87 (s, 1H), 7.78 (d, 1H), 7.57 (s, 1H), 7.28 to 7.35 (m, 5H), 7.13 (d, 1H), 6.58 (s, 1H), 5.64 (s, 2H), 4.53 (t, 1H), 3.47 (q, 2H), 2.91 (t, 2H), 1.82 to 1.86 (m, 2H); LC-MS [M+H]P=399, RT=2.41 min.

Provenance & Evidence