5-Methoxy-2-methylindole → HCID 19041729, compound

HRID 1684005Notes

Reaction equation

HRID 1684005 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][C:7]([O:11][CH3:12])=[CH:6][CH:5]=2.Br[CH2:14][C:15]1[CH:24]=[CH:23][CH:22]=[CH:21][C:16]=1[C:17]([O:19][CH3:20])=[O:18]>O1CCOCC1.CCOC(C)=O.[Ag-]=O>[CH3:12][O:11][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[NH:3][C:2]([CH3:1])=[C:10]2[CH2:14][C:15]1[CH:24]=[CH:23][CH:22]=[CH:21][C:16]=1[C:17]([O:19][CH3:20])=[O:18]

Participants

6

Reactant 2

HCID 706425-Methoxy-2-methylindoleHCID 2734813Methyl 2-(bromomethyl)benzoate

Product 1

HCID 19041729HCID 19041729, compoundYield 21.2%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
50 °C

Procedure

A mixture of 2-methyl-5-methoxy indole (1.01 g, 6.2 mmol), methyl 2-(bromomethyl)benzoate (1.60 g, 6.9 mmol) and silver (I) oxide (1.59 g, 6.9 mmol) in dioxane (8 mL) was heated to 50° C. for 20 h. The mixture was cooled, diluted with EtOAc and filtered thorugh celite. The filtrate was concentrated and the resulting residue was chromatographed to give 406 mg of the title compound.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered thorugh celite
  3. concentrationThe filtrate was concentrated
  4. customthe resulting residue was chromatographed

Sources & evidence

ORD record
ord-745a61efc1e84f26a352cdfde5960ed3
Source dataset
uspto-grants-1997_06
Patent number
US05639780

Reaction notes

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