2-Fluoroethyl bromide → HCID 89662821, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of Example 144 (100 mg; 0.23 mmol; 1 eq.), 1-bromo-2-fluoro-ethane (47 mg; 0.37 mmol; 1.6 eq.) and NaHCO3 (193 mg; 2.29 mmol; 10 eq.) in DMF was stirred at 100° C. for 30 minutes. 1-Bromo-2-fluoro-ethane (47 mg; 0.37 mmol; 1.6 eq.) was added and the resulting mixture was stirred at 100° C. for 30 minutes then concentrated in vacuo. After dilution with EA, the solution was washed with sat. aq. NaHCO3 then brine, dried over magnesium sulfate and concentrated in vacuo. Purification by column chromatography (EA to 10% MeOH in EA) afforded the title compound (50 mg, 49%) as a white foam. 1H NMR (DMSO-d6) δ 7.51-7.39 (m, 1H), 7.36-7.24 (m, 1H), 7.15 (d, J=8.3 Hz, 1H), 7.04 (t, J=7.3 Hz, 1H), 4.80 (d, J=7.3 Hz, 2H), 4.59 (d, J=19.7 Hz, 2H), 4.37 (td, J=5.0, 3.2 Hz, 1H), 4.21 (td, J=5.1, 3.3 Hz, 1H), 4.12 (t, J=5.3 Hz, 2H), 2.84 (s, 2H), 2.81 (s, 1H), 2.71 (t, J=5.2 Hz, 2H), 2.67-2.60 (m, 2H), 2.60-2.53 (m, 2H), 2.15 (s, 3H). HPLC (max plot) 97.5%, Rt 2.65 min. UPLC/MS: (MS+) 446.2 ([M+H]+).

Provenance & Evidence