Ammonium Chloride → Ethyl 2-(5-amino-4-fluoro-2-(2-(trimethylsilyl)ethynyl)phenyl)acetate

Participants

Reaction Steps

To a stirring suspension of ethyl 2-(4-fluoro-5-nitro-2-(2-(trimethylsilyl)ethynyl)phenyl)acetate (0.66 g, 2.04 mmol) in MeOH/THF (1:1, 20 mL) was added NH4Cl (1.09 g, 20.4 mmol), followed by Zn dust (1.33 g, 20.4 mmol). After stirring 1.5 h, the mixture was filtered through C elite, and rinsed forward with MeOH. The combined filtrates were concentrated, diluted with brine and extracted with THF (2×). The combined organic layers were washed with brine (1×), dried (MgSO4), filtered and concentrated to afford ethyl 2-(5-amino-4-fluoro-2-(2-(trimethylsilyl)ethynyl)phenyl)acetate (0.54 g, 90% yield). 1H NMR (400 MHz, DMSO-d6): δ 6.86 (d, J=12.0 Hz, 1H), 6.47 (d, J=8.8 Hz, 1H), 5.47 (brs, 2H), 3.88 (d, J= 6.8 Hz, 2H), 3.43 (s, 2H), 1.00 (d, J=6.8 Hz, 3H), 0.00 (s, 9H); MS (ESI) m/z: 294.0 (M+H+).

Provenance & Evidence