Water → 5-Bromo-7-(4-bromobutyl)pyrrolo[2,1-f][1,2,4]triazin-4-amine

Participants

Reaction Conditions

Reaction Steps

To a cooled (0° C.) solution of 4-(4-amino-5-bromopyrrolo[2,1-f][1,2,4]triazin-7-yl)butan-1-ol (600 mg, 2.10 mmol) and triphenylphosphine (828 mg, 3.16 mmol) in tetrahydrofuran (15 mL) was added carbon tetrabromide (837 mg, 2.53 mmol). The reaction was stirred (0° C.) for 90 min and then was warmed to rt and stirred an additional 1 h. Water (25 mL) was added and the mixture was extracted with ethyl acetate (2×25 mL). The combined organics were dried (Na2SO4) and evaporated. The crude material was purified via ISCO® chromatography using a gradient of 25 to 50% ethyl acetate in hexanes to afford 597 mg (82%) of the desired product. 1H NMR (300 MHz, DMSO-d6) δ 7.82 (s, 1 H), 6.62 (s, 1 H), 3.54 (t, 2 H), 2.84 (t, 2 H), 1.86-1.70 (m, 4 H); ES-MS m/z 347.2 [M+H]+, HPLC RT (min) 2.58.

Provenance & Evidence