Diazomethane → methyl 1H-indole-4-carboxylate

HRID 247854

Reaction equation

HRID 247854 reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([C:10]([OH:12])=[O:11])[C:4]=2[CH:3]=[CH:2]1.[N+](=[CH2:15])=[N-].S([O-])([O-])(=O)=O.[Mg+2]>CO.C(OCC)C>[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([C:10]([O:12][CH3:15])=[O:11])[C:4]=2[CH:3]=[CH:2]1

Participants

6

Reactant 3

HCID 9550DiazomethaneHCID 24083Sulfuric acid magnesium salt (1:1)HCID 595229Indole-4-carboxylic acid

Product 1

HCID 2733668methyl 1H-indole-4-carboxylateYield 98%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of indole-4-carboxylic acid (506 mg, 3.14 mmol) dissolved in a mixture of methanol (5 mL) and diethyl ether (10 mL) was added ethereal diazomethane until disappearance of the starting acid was indicated by TLC. Magnesium sulfate was then added and the solution filtered and concentrated in vacuo. Flash chromatography on Merck silica gel (10 g) eluted with 2:1, chloroform:hexanes, followed by 10:1, chloroform: ether afforded the title compound (540 mg, 98%).

Workup

  1. filtrationthe solution filtered
  2. concentrationconcentrated in vacuo
  3. washFlash chromatography on Merck silica gel (10 g) eluted with 2:1, chloroform

Sources & evidence

ORD record
ord-f3eca2e7cd8b4af0b2f619fef1d40c9d
Source dataset
uspto-grants-1993_05
Patent number
US05208235

Linked notes

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