反应详情

A stirred mixture of 4-(3-cyclopentyloxy-4-methoxyphenyl)-4-ethynylcyclohexan-1-one (0.100 g, 0.32 mmol) and 5-(3-iodophenyl)-2-methyl-[1,3,4]oxadiazole (0.0915 g, 0.32 mmol) in dry triethylamine (3.5 mL) was treated under argon with a mixture of tetrakis(triphenylphosphine)palladium (0.016 g, 0.013 mmol), cuprous iodide (0.0033 g, 0.017 mmol), and triphenylphosphine (a small crystal) at 75° C. for 1 h. The reaction mixture was concentrated in vacuo, the residue was extracted into methylene chloride and the organic phase was washed with cold dilute hydrochloric acid, water, brine and was dried (sodium sulfate). Purification by chromatography (silica, 10 to 20% ethyl acetate in methylene chloride) followed by drying at 50° C. in vacuo afforded the titled compound as a white powder (0.068 g, 45%), mp 139°-141° C. Anal. (C29H30N2O4.1/3H2O) calcd: C 73.09, H 6.49, N 5.88, found: C 73.07, H 6.35, N 5.79. 1H-NMR (400 MHz, CDCl3) δ 8.15 (t, J=1.6 Hz, 1H), 8.01 (d-t, J=1.4 Hz, J=7.9 Hz, 1H), 7.62 (d-d, J=1.5 Hz, J=7.8 Hz, 1H), 7.49 (t, J=7.9 Hz), 7.21 (d, J=2.3, 1H), 7.14 (d-d, J=8.5 Hz, J=2.4 Hz, 1H), 6.88 (d, J=8.5, 1H), 4.82 (p, J=4.2 Hz, 1H), 3.86 (s, 3H), 3.04 (d-t, J=6.1 Hz, J=14.2, 2H), 2.64 (s, 3H), 2.51 (d,br, J=15.0, 2H), 2.42-2.32 (m, 2H), 2.27 (d-t, J=2.8 Hz, J=14.2 Hz, 2H), 2.00-1.5 (m, 9H with H2O).

1. concentrationThe reaction mixture was concentrated in vacuo
2. extractionthe residue was extracted into methylene chloride
3. washthe organic phase was washed with cold dilute hydrochloric acid, water, brine
4. dry with materialwas dried (sodium sulfate)
5. customPurification by chromatography (silica, 10 to 20% ethyl acetate in methylene chloride)
6. customby drying at 50° C. in vacuo