Tetrabutylammonium Fluoride → HCID 72725463, compound

Participants

Reaction Steps

To a solution of N-(6-((tert-butyldimethylsilyl)oxy)-4,5,6,7-tetrahydrobenzo[d]thiazol-2-yl)-4-(6-fluoroindolin-1-yl)piperidine-1-carboxamide (106 mg, 0.2 mmol) in THF (3 mL) was added TBAF solution (1.0 M in THF, 0.8 mL, 0.8 mmol, 4 equiv) at room temperature. The resulting mixture was stirred at room temperature for 24 h and was poured into EtOAc/H2O (20 mL/20 mL). The organic layer was washed with brine (20 mL), dried (Na2SO4), and filtered. The solvent was removed by roto-evaporator and the resulting residue purified by column using 70-90% EtOAc/hexane as the eluent to yield 4-(6-fluoroindolin-1-yl)-N-(6-hydroxy-4,5,6,7-tetrahydrobenzo[d]thiazol-2-yl)piperidine-1-carboxamide as a white solid.

Provenance & Evidence