Trifluoroacetic acid → HCID 42610584, compound

Participants

Reaction Steps

Synthesis of 3-(4-Fluoro-benzyl)-6-methoxy-3′-nitro-biphenyl-2-ol (P-099) In an 8 mL vial equipped with a stir bar was placed I-246 (60 mg, 0.163 mmol) and triethylsilane (350 μL). The mixture was cooled in an ice-water bath and then TFA (350 μL) was added. The reaction mixture was warmed to room temperature and reacted for 17 hours. After this time period, additional triethylsilane (1.1 mL) and TFA (1.1 mL) was introduced and the reaction mixture was heated to 60° C. in an oil bath for 24 hours. The reaction mixture was concentrated by a stream of N2, quenched with water (20 mL) and extracted with dichloromethane (2×30 mL). The organic portions were combined, washed with brine (30 mL), dried (MgSO4) and concentrated. The residue was purified by SiO2 column chromatography utilizing 15% EtOAc/hexanes as the eluent to produce 18.9 mg of P-099 as a viscous, tan oil in 33% yield. 1H NMR (400 MHz, CDCl3) δ 3.72 (s, 3H), 3.94 (s, 2H), 4.73 (s, 1H), 6.55 (d, J=8 Hz, 1H), 6.96-7.00 (m, 2H), 7.01 (d, J=8 Hz, 1H), 7.19-7.22 (m, 2H), 7.63 (t, J=7 Hz, 1H), 7.69 (dt, J=8, 2 Hz, 1H), 8.22-8.26 (m, 2H) ppm. MS (APCI−): 352.1 (M−1); LC-MS: 98%.

Provenance & Evidence