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

HRID 2073552Notes

Reaction equation

HRID 2073552 reaction equation
[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

Participants

6

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 178418778HCID 178418778, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-a2e8b2d0524445e39da427fe277993d0
Source dataset
uspto-grants-1990_04
Patent number
US04918094

Reaction notes

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