1-[(4-Fluoro-1-naphthyl)sulfonyl]-1,2,3,4-tetrahydroquinoline—Method E: To a stirred solution of 4-fluoronaphthalene-1-sulfonyl chloride (200 mg, 0.82 mmol) in DCM (1 ml) was added 1,2,3,4-tetrahydroquinoline (123 μl, 0.98 mmol) followed by pyridine (0.25 ml). The reaction mixture was stirred over night, diluted with DCM and washed with 1M HCl (3×3 ml). Subsequent drying of the organic phase using MgSO4, and removal of the solvents in vacuo afforded the title compound (280 mg, 100%) as a white solid. 1H NMR (CDCl3) δ 8.24–8.10 (m, 3H), 7.68–7.62 (m, 1H), 7.58–7.51 (m, 1H), 7.42–7.34 (m, 1H), 7.23–7.04 (m, 3H), 6.96–6.89 (m, 1H), 3.84–3.74 (m, 2H), 2.39–2.28 (m, 2H), 1.63–1.49 (m, 1H); MS m/z (M+1) 342.
