Methyl 4-(bromomethyl)-3-methoxybenzoate → Methyl 4-[5-[N-(cyclopentylmethyl)-N-methylcarbamoyl]-1-methylindol-3-ylmethyl]-3-methoxybenzoate

HRID 728682

反応式

HRID 728682 の反応式
[CH:1]1([CH2:6][N:7]([CH3:20])[C:8]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[N:15]([CH3:19])[CH:14]=[CH:13]3)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.Br[CH2:22][C:23]1[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][C:24]=1[O:33][CH3:34]>O1CCOCC1.C(OCC)(=O)C.[Ag-]=O>[CH:1]1([CH2:6][N:7]([CH3:20])[C:8]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[N:15]([CH3:19])[CH:14]=[C:13]3[CH2:22][C:23]2[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][C:24]=2[O:33][CH3:34])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

6

反応物 2

HCID 2759828Methyl 4-(bromomethyl)-3-methoxybenzoateHCID 198224715-[N-(cyclopentylmethyl)-N-methylcarbamoyl]-1-methylindole

生成物 1

HCID 19822472Methyl 4-[5-[N-(cyclopentylmethyl)-N-methylcarbamoyl]-1-methylindol-3-ylmethyl]-3-methoxybenzoate収率 13.2%

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2 回

実験手順

Silver(I) oxide (0.30 g) was added to a solution of 5-[N-(cyclopentylmethyl)-N-methylcarbamoyl]-1-methylindole (G) (0.35 g) in dioxane (2 ml). The mixture was protected from light, stirred, and heated to reflux under an atmosphere of nitrogen for 2 hours. A solution of methyl 4-bromomethyl-3-methoxybenzoate (B) (0.33 g) in dioxane (1 ml) was added and the mixture was heated to reflux for an additional 18 hours. The mixture was then diluted with ethyl acetate and filtered. The filtrate was evaporated to give an amber gum which was purified by flash chromatography on silica gel (223 ml), eluting with chloroform to give the title compound (75.2 mg, 13%) as a white foam; partial nmr (80 MHz, CDCl3): 3.01(s, 3H, CONCH3), 3.51(br d, 2H, NCH2), 3.74(s, 3H, NCH3), 3.89(s, 3H, OCH3), 3.92(s, 3H, OCH3), 4.10(s, 2H, ArCH2), 6.81(s, 1H, H2 -indole).

後処理

  1. temperatureheated
  2. temperatureto reflux under an atmosphere of nitrogen for 2 hours
  3. temperaturethe mixture was heated
  4. temperatureto reflux for an additional 18 hours
  5. filtrationfiltered
  6. customThe filtrate was evaporated
  7. customto give an amber gum which
  8. customwas purified by flash chromatography on silica gel (223 ml)
  9. washeluting with chloroform

出典と根拠

ORDレコード
ord-c9fe621e7a3342c48fd04c1ea3b4ba1b
出典データセット
uspto-grants-1991_09
特許番号
US05049679

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