Hydrochloric Acid → (1-Benzyl-1H-indazol-5-yl)-(6-(1-methylpyrrol-2-yl)-quinazolin-4-yl)-amine hydrochloride

Participants

Reaction Steps

A stirred solution of 1-methyl-2-(tri-n-butylstannyl)pyrrole (prepared as described in H. M. R. Hoffmann et al. Synthesis, 1996, 164) (1.07 g, 2.89 mmol), (1-benzylindazol-5-yl)-(6-iodoquinazolin-4-yl)-amine hydrochloride (1.0 g, 1.95 mmol), triethylamine (0.4 ml , 0.29 g, 2.87 mmol) and 1,4-bis(diphenylphosphino)-butane palladium (II) chloride (0.1 g, catalytic) in dioxane (10 ml) was heated to reflux under a nitrogen atmosphere for 18 hours. The mixture was concentrated in vacuo and purified by silica gel chromatography, eluting with 2:1 i-hexane/EtOAc. Concentration of the appropriate fractions gave a yellow solid which was dissolved in EtOAc and treated with a solution of HCl in dioxane. The precipitate was collected by filtration, washed with EtOAc and dried at 60C in vacuo to give the product as a green-yellow solid (0.26 g, 0.557 mmol, 29%); δH [2H6]DMSO 11.95 (1H, s), 8.86-8.96 (2H, m), 8.18-8.27 (2H, m), 8.07 (1H, s), 7.99 (1H, d), 7.83 (1H, d), 7.65 (1H, dd), 7.22-7.40 (5H, m), 7.01 (1H, t), 6.49 (1H, dd), 6.19 (1H, t), 5.71 (2H, s), 3.82 (3H, s); m/z (M+1+) 431.

Provenance & Evidence