反応式
CO[C:3](=[O:23])[C:4]([C:6]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:12][CH:13]=2)[NH:8][CH:7]=1)=O.[CH3:24][N:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][C:32]=2[CH2:34][C:35]([NH2:37])=[O:36])[CH:27]=[CH:26]1.C(O[K])(C)(C)C>C1COCC1>[CH2:16]([O:15][C:11]1[CH:10]=[C:9]2[C:14]([C:6]([C:4]3[C:3](=[O:23])[NH:37][C:35](=[O:36])[C:34]=3[C:32]3[CH:31]=[CH:30][CH:29]=[C:28]4[C:33]=3[N:25]([CH3:24])[CH:26]=[CH:27]4)=[CH:7][NH:8]2)=[CH:13][CH:12]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1参加物
実験手順
To a suspension of (6-benzyloxy-1H-indol-3-yl}-oxo-acetic acid methyl ester (1.0 g, 3.2 mmol) and 2-(1-methyl-1H-indol-7-yl)-acetamide (608 mg, 3.2 mmol) in 15 ml THF was added 3.5 equiv. of tBuOK in THF at 0° C. (11.3 ml of 1.0 M solution in THF) under N2. The mixture was stirred at r.t overnight, quenched with conc. HCl 5.0 ml, and neutralized with 5 N NaOH to PH=8. The mixture was extracted with ethyl acetate, and the extract was washed with saturated NaHCO3, brine and water, dried over anhydrous MgSO4, filtered and concentrated. The residue was purified by flash chromatography with Hexane:Ethyl acetate (1:1) to yield the title compound (700 mg) as orange solid, 74% yield. MS(m/z): 448.2 (M++1), 446.1 (M−−1); 1HNMR (DMSO-d6) 11.62 (s, 1H), 11.07 (s, 1H), 7.77 (d, J=1.80 Hz, 1H), 7.57 (m, 1H ), 7.26 (m, 5H), 7.21 (d, J=2.40 Hz, 1H), 6.94 (tri, J=6.00 Hz, 1H), 6.84 (m, 2H), 6.44(d, J=2.40 Hz, 1H), 6.16 (s, 1H), 4.97 (s, 2H), 3.62 (s, 3H).
後処理
- customquenched with conc. HCl 5.0 ml
- extractionThe mixture was extracted with ethyl acetate
- washthe extract was washed with saturated NaHCO3, brine and water
- dry with materialdried over anhydrous MgSO4
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by flash chromatography with Hexane:Ethyl acetate (1:1)
出典と根拠
- ORDレコード
- ord-e4bbb6fa380443e0aca38ac8e82bab94
- 出典データセット
- uspto-grants-2006_09
- 特許番号
- US07109229B2
関連ノート
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