Diazomethane → Methyl indole-6-carboxylate

HRID 1982919Notes

Reaction equation

HRID 1982919 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 MDC 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-03894f12e5284b38822fdaa3aa8e95c6
Source dataset
uspto-grants-2009_06
Patent number
US07541351B2

Reaction notes

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