Monochloramine → 5-Fluoro-1H-indol-1-amine

Participants

Reaction Steps

A solution of 5-fluoro-1H-indole (16.9 mmol) and potassium tert-butoxide (33.8 mmol) in DMF (76 mL) is stirred at rt under N2 for 2 h. 0.15 M NH2Cl. in ether (169.2 mL) is added drop-wise for 15 minutes at rt. The reaction mixture is stirred at rt for 2 h, then quenched with 10% Na2S2O3 aqueous solution and extracted with ether. The organic layer is separated, dried (Na2SO4), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 60-80% EtOAc in heptane to afford 5-fluoro-indole-1-ylamine (751 mg, 30%) as a solid. 1H NMR (300 MHz, CDCl3): δ 4.80 (br, 2N—H), 6.38 (d, H), 7.00 (m, H), 7.19-7.43 (m, 3H).

Provenance & Evidence