Tetrabutylammonium Fluoride → HCID 58266582, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3-chloro-9-(2-trimethylsilanylethoxymethyl)-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (24.2 mg, 67.4 μmol) in THF (1.3 mL) was treated with TBAF (398 μL, 1.35 mmol) and heated to 60° C. for 2 h. The reaction mixture was cooled to ambient temperature and the solvent removed in vacuo. The resultant residue was dissolved in DCM/EtOAc, absorbed onto silica gel, and purified by flash chromatography (silica, 4 g column, Biotage, 1-20% methanol in DCM containing 0 1% 7N ammonia in MeOH). Collecting appropriate fractions afforded a solid which was further purified by preparative HPLC (5-85% MeCN in water (0.1% NH4OH) over 30 min, 35 mL/min) to afford the title compound as an off-white solid (10 mg, 66%). 1H NMR (400 MHz, DMSO-D6): 13.07 (s, 1H), 9.05 (d, J=0.9 Hz, 1H), 8.95 (d, J 2.4 Hz, 1H), 8.92 (d, J=0.9 Hz, 1H), 8.73 (d, J=2.4 Hz, 1H). LCMS (Method E): RT=3.98 min, M+H+=229.

Provenance & Evidence