Tetrahydrofuran → HCID 84076342, compound

Participants

Reaction Steps

A mixture of 5-fluoro-1H-indole-4-carboxamide (240 mg, 1.35 mmol) and a solution of BH3 in THF (1.0 M, 16 mL, 16 mmol) was stirred at RT for 18 hours. The reaction was quenched with a solution of HCl (1.0 M, 20 mL) followed by stirring at RT for 1.5 h. The pH of the reaction mixture was adjusted to about ca. 10 by adding a satd. aq. Na2CO3. The mixture was extracted with EtOAc (50 mL×3). The combined organic layers were washed with water and brine, dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by SiO2 chromatography eluting with DCM/MeOH/TEA (10:1:0.1) to afford (5-fluoro-1H-indol-4-yl)methanamine (107) as a yellow solid (190 mg, 86.4%). MS (ESI): m/z=148.1 [M−16]+.

Provenance & Evidence