反応 #930307

反応方程式

4-(3-bromo-propoxy)-3-cyclopropyl-benzofuran-2-carboxylic acid ethyl ester

3-aminomethylpyridine

→

3-cyclopropyl-4-{3-[(pyridin-3-ylmethyl)-amino]-propoxy}-benzofuran-2-carboxylic acid ethyl ester

溶媒

ethyl acetate

ethanol

反応条件

後処理

1. 1
   洗浄washed with saturated aqueous ammonium chloride solution (5 ml) and water (5 ml)
2. 2
   乾燥dried over anhydrous sodium sulfate
3. 3
   濃縮concentrated in vacuo to dryness
4. 4
   その他The residue was purified by silica gel column chromatography

実験手順

To a solution of 4-(3-bromo-propoxy)-3-cyclopropyl-benzofuran-2-carboxylic acid ethyl ester (92 mg) in ethanol (4 ml) was added 3-aminomethylpyridine (500 μl) and heated at 70° C. overnight. The mixture was diluted with ethyl acetate (10 ml) and washed with saturated aqueous ammonium chloride solution (5 ml) and water (5 ml), then dried over anhydrous sodium sulfate, concentrated in vacuo to dryness. The residue was purified by silica gel column chromatography developed by dichloromethane-methanol to give 3-cyclopropyl-4-{3-[(pyridin-3-ylmethyl)-amino]-propoxy}-benzofuran-2-carboxylic acid ethyl ester as a pale yellow oil (108 mg). ESI-MS: m/z 395 (MH+); 1H-NMR (CDCl3): δ 0.95-1.08 (4H, m), 1.44 (3H, t, J=7.3 Hz), 2.10 (2H, quintet, J=6.3 Hz), 2.54-2.60 (1H, m), 2.89 (2H, t, J=6.3 Hz), 3.85 (2H, s), 4.17 (2H, t, J=6.3 Hz), 4.45 (2H, q, J=7.3 Hz), 6.63 (1H, d, J=7.9 Hz), 7.13 (1H, d, J=7.9 Hz), 7.21-7.34 (2H, m), 7.68 (1H, d, J=7.9 Hz), 8.48 (1H, dd, J=1.7 Hz, 4.9 Hz), 8.56 (1H, d, J=1.7 Hz).

出典