Water → HCID 22663283, compound

HRID 392218Notes

Reaction equation

HRID 392218 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:9]=2)[NH:4][CH:3]=1.Br[CH2:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[OH-].[Na+].O>CC(C)=O>[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:9]=2)[N:4]([CH2:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 12503(3-Bromopropyl)benzeneHCID 14798Sodium HydroxideHCID 21938240Methyl 3-methyl-1H-indole-6-carboxylate

Product 1

HCID 22663283HCID 22663283, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A stirred solution of methyl 3-methyl-1H-indole-6-carboxylate (0.5 g, Reference Example 30) in acetone (35 ml) was treated with 1-bromo-3-phenylpropane (0.577 g) and sodium hydroxide (0.116 g). The mixture was stirred at room temperature for 12 hours then poured into water (35 ml) and then extracted three times with ethyl acetate (50 ml). The combined extracts were washed with dilute hydrochloric acid (50 ml, 1N) then with saturated sodium bicarbonate solution (50 ml), then dried over magnesium sulphate and then evaporated. The residue was subjected to flash column chromatography on silica eluting with a mixture of ethyl acetate and hexane (50:1, v/v) to yield the title compound (0.58 g).

Workup

  1. extractionextracted three times with ethyl acetate (50 ml)
  2. washThe combined extracts were washed with dilute hydrochloric acid (50 ml, 1N)
  3. dry with materialwith saturated sodium bicarbonate solution (50 ml), then dried over magnesium sulphate
  4. customevaporated
  5. additionThe residue was subjected to flash column chromatography on silica eluting with a mixture of ethyl acetate and hexane (50:1

Sources & evidence

ORD record
ord-cf19aed7c5ba4e4588005a85384c3bfe
Source dataset
uspto-grants-2004_10
Patent number
US06800645B1

Reaction notes

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