2-Fluoroethyl bromide → HCID 19601672, compound

Participants

Reaction Steps

To a solution of 1-(2-iodophenyl)-N-methyl-3-isoquinolinecarboxamide (0.1042 g, 0.27 mmol) in DMF (6 mL) was added 60% NaH (43 mg, 1.08 mmol) in one portion. The mixture was stirred under Ar at room temperature for 30 min before 2-fluoroethylbromide (161 μl, 2.16 mmol) was added in one portion. The mixture was stirred at room temperature under Ar for 20 h, then quenched by adding H2O (5 mL). The mixture was extracted with CH2Cl2 (3×15 mL). The combined organic layers were dried (MgSO4), and filtered. The filtrate was concentrated in vacuo. The residue was purified on flash column chromatography (SiO2 , 30% ethyl acetate/hexane, 0.035% Et3N). A white solid (48 mg, 41%) was obtained. mp 141.9-143.2° C. 1H NMR (CDCl3) d 3.22, 3.27 (two s, 3 H, N-methyl), 3.67-4.15 (m, 2 H, N--CH2), 4.42-4.92 (m, 2 H, CH2F), 7.15-7.25 (m, 1 H, aromatic), 7.27-7.37 (m, 1 H, aromatic), 7.45-7.64 (m, 3 H, aromatic), 7.67-7.77 (m, 1 H, aromatic), 7.97 (t, J=7.5 Hz, 2 H, aromatic), 8.11, 8.21 (two s, total 1 H, aromatic). Anal. Calcd for Cl19H16FIN2O: C, 52.55; H, 3.71; N, 6.45. Found: C, 52.64; H, 3.78; N, 6.38.

Provenance & Evidence