Tetrabutylammonium Fluoride → HCID 71285864, compound

Participants

Reaction Steps

In a round-bottomed flask containing 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-1-(4-cyanophenyl)-ethyl]-amide (32 mg, 0.056 mmol) dissolved in THF (1 ml) was added TBAF (1.0 M in THF, 1.0 ml, 1.0 mmol). The flask was backfilled with nitrogen then sealed and placed in an oil bath at 85° C. for 2 h. The reaction was cooled to room temperature, quenched with acetone (2 ml) and sat'd NaHCO3 (4 ml). The mixture was stirred for 1 h then diluted with water and extracted with EtOAc. Brine was added and the aqueous layer was extracted twice with EtOAc. The combined organics were washed with water and brine then dried over MgSO4, filtered and concentrated. The crude solid was purified by flash chromatography (4 g silicycle) with 0% to 7.5% MeOH in dichloromethane. The appropriate fractions were combined and concentrated to afford 4 mg (19%) of 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-1-(4-cyano-phenyl)-ethyl]-amide as a white solid. LC-MS (M+H)+=440; 1H NMR (300 MHz, DMSO-d6) δ: 12.97 (br. s., 1H), 9.17 (s, 1H), 8.33-8.69 (m, 3H), 7.85 (d, J=8.3 Hz, 2H), 7.64-7.78 (m, 3H), 7.08 (d, J=2.0 Hz, 1H), 5.39 (br. s., 1H), 4.20 (s, 3H), 1.70 (d, J=7.0 Hz, 3H).

Provenance & Evidence