Diazomethane → methyl 1H-indole-4-carboxylate

HRID 52160

Reaction equation

HRID 52160 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 starting acid was indicated by TLC. Anhydrous magnesium sulfate was then added and the solution filtered and concentrated in vacuo. Flash chromatography on 10 g of Merck silica gel eluted with 2:1, chloroform:hexanes, followed by 10:1, chloroform:diethyl ether afforded the title compound (540 mg, 98%).

Workup

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

Sources & evidence

ORD record
ord-5d171451110d4124a3baf16313134425
Source dataset
uspto-grants-1997_04
Patent number
US05616591

Linked notes

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