Water → HCID 58529843, compound

Participants

Reaction Conditions

Reaction Steps

To a cooled (0° C.) solution of 4{4-amino-5-[3-(benzyloxy)phenyl]pyrrolo[2,1-f][1,2,4]triazin-7-yl}butan-1-ol (489 mg, 1.26 mmol) and triphenylphosphine (495 mg, 1.89 mmol) in tetrahydrofuran (8 mL) was added carbon tetrabromide (501 mg, 1.51 mmol). The reaction was stirred (0° C.) for 2 h and was then warmed to rt and stirred an additional 17 h. Water (25 mL) was added and the mixture was extracted with ethyl acetate (2×20 mL). The combined organics were washed with brine, 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 484 mg (85%) of the desired product. 1H NMR (300 MHz, DMSO-d6) δ7.88 (s, 1 H), 7.46-7.42 (m, 2 H), 7.41-7.28 (m, 4 H), 7.08-7.05 (m, 1 H), 7.03-6.97 (m, 2 H), 6.57 (s, 1 H), 5.14 (s, 2 H), 3.57 (t, 2 H), 2.90 (t, 2 H), 1.92-1.77 (m, 4 H); ES-MS m/z 451.1 [M+H]+, HPLC RT (min) 3.22.

Provenance & Evidence