Borane;tetrahydrofuran → HCID 59395056, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-amino-3-hydroxy-3-(trifluoromethyl)indolin-2-one (58 mg, 0.25 mmol) in anhydrous THF (0.5 mL) at 0° C. was added BH3.THF complex (1M in THF) (1 mL, 0.95 mmol, 4 eq) dropwise. The mixture was stirred for 5 min at 0° C. then for 3 h at room temperature. The reaction was quenched by adding very carefully 6M HCl (3.5 mL) until no more gas release was observed. The mixture was then stirred at 80° C. for 2 h. The solvent was removed under reduce pressure and the solid residue obtained was dissolved in DMF (3 mL), filtered and purified by reverse phase HPLC (10-99% ACN in water) to give 3-(trifluoromethyl)-1H-indol-6-amine (30 mg, 54%, TFA salt).

Provenance & Evidence