Diazomethane → Methyl indole-6-carboxylate

HRID 1723937Notes

Reaction equation

HRID 1723937 reaction equation
[N+](=[CH2:3])=[N-].[NH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]([OH:15])=[O:14])[CH:11]=2)[CH:6]=[CH:5]1>C(OCC)C>[NH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]([O:15][CH3:3])=[O:14])[CH:11]=2)[CH:6]=[CH:5]1

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 5952301H-indole-6-carboxylic acid

Product 1

HCID 639844Methyl indole-6-carboxylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

An ethereal solution of diazomethane (620 mL) was added slowly to a cooled, (−15° C.) stirred suspension of 6-indole carboxylic acid (45 g, 0.27 mol.) in diethyl ether (250 mL). Upon addition, the reaction mixture was stirred for a further 1 h at −15° C., after which the reaction was quenched by the slow addition of acetic acid (50 mL). The resultant mixture was then concentrated under reduced pressure, and the residue purified using flash chromatography on silica (60-120), using DCM as eluant.

Workup

  1. additionUpon addition
  2. stirringthe reaction mixture was stirred for a further 1 h at −15° C.
  3. customafter which the reaction was quenched by the slow addition of acetic acid (50 mL)
  4. concentrationThe resultant mixture was then concentrated under reduced pressure
  5. customthe residue purified

Sources & evidence

ORD record
ord-429b071736184fc6b5eca5eb1b217018
Source dataset
uspto-grants-2009_02
Patent number
US07485633B2

Reaction notes

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