Methyl 4-(bromomethyl)-3-methoxybenzoate → Methyl 4-[1-(2-carbamoylethyl)-5-(N-cyclopentylmethylcarbamoyl)indol-3-ylmethyl]-3-methoxybenzoate

HRID 728673

反応式

HRID 728673 の反応式
[C:1]([CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([C:15](=[O:23])[NH:16][CH2:17][CH:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[CH:12][CH:13]=2)[CH:8]=[CH:7]1)(=[O:3])[NH2:2].Br[CH2:25][C:26]1[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:28][C:27]=1[O:36][CH3:37]>O1CCOCC1.C(OCC)(=O)C.[Ag-]=O>[C:1]([CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([C:15](=[O:23])[NH:16][CH2:17][CH:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[CH:12][CH:13]=2)[C:8]([CH2:25][C:26]2[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:28][C:27]=2[O:36][CH3:37])=[CH:7]1)(=[O:3])[NH2:2]

参加物

6

反応物 2

HCID 2759828Methyl 4-(bromomethyl)-3-methoxybenzoateHCID 198224771-(2-carbamoylethyl)-5-(N-cyclopentylmethylcarbamoyl)indole

生成物 1

HCID 19822473Methyl 4-[1-(2-carbamoylethyl)-5-(N-cyclopentylmethylcarbamoyl)indol-3-ylmethyl]-3-methoxybenzoate収率 39%

試薬・触媒・溶媒 3

HCID 178418778HCID 178418778、化合物触媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

Silver(I) oxide (0.17 g) was added to a solution of 1-(2-carbamoylethyl)-5-(N-cyclopentylmethylcarbamoyl)indole (0.70 g) and methyl 4-bromomethyl-3-methoxybenzoate (B)(0.19 g) in 1,4-dioxane (10 ml). The mixture was protected from light and stirred at 80° C. under an atmosphere of nitrogen for 12 hours. The mixture was then diluted with 1:1 v/v ethyl acetate:ether (50 ml) and filtered. The filtrate was washed sequentially with water and brine, dried (MgSO4), and evaporated. The residual yellow gum was purified by flash chromatography on silica gel (500 ml), eluting with 5:95 v/v methanol:chloroform to give the title compound (0.14 g, 39%) as a white solid; mp 189°-191° C. (d); NMR (250 MHz, DMSO-d6): 1.2-1.8(broad m, 8H, cyclopentyl), 2.2(sep, 1H, cyclopentylmethine), 3.2(t, 2H, CH2NH), 7.2(m, 2H), 7.3(broad s, 1H, CONH2), 7.5 (m, 3H), 7.7(d, 1H, H6 -indole), 8.0(s, 1H, H4 -indole), 8.3(t, 1H, NHCO).

後処理

  1. filtrationether (50 ml) and filtered
  2. washThe filtrate was washed sequentially with water and brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residual yellow gum was purified by flash chromatography on silica gel (500 ml)
  6. washeluting with 5:95 v/v methanol

出典と根拠

ORDレコード
ord-52361734dd5344259ca8db06edd05715
出典データセット
uspto-grants-1991_09
特許番号
US05049679

関連ノート

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