Boron tribromide → HCID 57962073, compound

Participants

Reaction Steps

A solution of 6-chloro-12-methoxy-2,4,8,22-tetraazatetracyclo[14.3.1.1(3,7).1(9,13)]docosa-1(20),3(22),4,6,9(21),10,12,16,18-nonaene trifluoroacetate (157 mg, 0.34 mmol) in methylene chloride (2.5 mL) was cooled to −78° C. and 1 M boron tribromide in methylene chloride (1.68 mL, 1.68 mmol) was added slowly. The mixture was allowed to warm to room temperature and stir for 16 hours. The mixture was cooled to −78° C. and saturated sodium bicarbonate solution was added. The resulting suspension was filtered and the collected solid was washed with water and ethyl acetate to give the desired compound (113 mg, 100%). 1H NMR (300 MHz, DMSO-d6): δ 9.45 (s, 1H), 9.25 (s, 1H), 8.09 (s, 1H), 7.92 (s, 1H), 7.48 (s, 1H), 7.08 (m, 1H), 6.81 (m, 3H), 6.71 (d, 1H), 2.82 (s, 4H). LCMS for C18H16ClN4O (M+H)+: m/z=339.1.

Provenance & Evidence