Dimethylformamide → 5-(2-benzyl-2H-indazol-6-yl)-7H-pyrrolo[2,1-f][1,2,4]triazin-4-amine

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Reaction Steps

A stirred mixture of 5-bromopyrrolo[2,1-f][1,2,4]triazin-4-amine (100 mg, 0.47 mmol), 2-benzyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-indazole (188 mg, 0.56 mmol), sodium carbonate (119 mg, 1.13 mmol), N,N-dimethylformamide (4 mL) and water (0.3 mL) was degassed with nitrogen. Tetrakis(triphenylphosphine)palladium(0) (54 mg, 0.04 mmol) was added, and the reaction was irradiated in a microwave reactor at 150° C. for 15 minutes. The reaction mixture was filtered through Celite®, the pad washed with methanol, and the filtrate concentrated in vacuo. The residue was partitioned between dichloromethane and 1N aqueous hydrochloric acid. The dichloromethane extracts were washed with 5% aqueous sodium bicarbonate solution, then brine, dried (anhydrous sodium sulfate); filtered and concentrated in vacuo to afford 61 mg (38% yield) of yellow solid. 1H-NMR (CD2Cl2): δ 8.04 (d, 1 H), 7.86 (s, 1 H), 7.77 (dd, 1 H), 7.75 (d, 1 H), 7.65 (d; 1 H), 7.40-7.32 (m, 5 H), 7.21 (dd, 1 H), 6.77 (d, 1 H), 6.91 (br s, 2 H), 5,61 (s, 2 H). MS: LC/MS (+esi), m/z=341 [M+H]. RT=2.44 min.

Provenance & Evidence