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

HRID 2073552노트

반응식

HRID 2073552 반응식
[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

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 178418778HCID 178418778, 화합물촉매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

실험 절차

Silver(I) oxide (0.30 g) was added to a solution of 5-[N-(cyclopentylmethyl)-N-methylcarbamoyl]-1-methylindole (G) (0.35 g) in dixoane (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 additonal 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, HCH2), 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).

후처리

  1. temperatureheated
  2. temperatureto reflux under an atmosphere of nitrogen for 2 hours
  3. temperaturethe mixture was heated
  4. temperatureto reflux for an additonal 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

출처 및 근거

ORD 기록
ord-a2e8b2d0524445e39da427fe277993d0
출처 데이터셋
uspto-grants-1990_04
특허 번호
US04918094

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