Diazomethane → Methyl indole-6-carboxylate

HRID 1453344Notes

Reaction equation

HRID 1453344 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-74665c0564d44e96941f486b86fcb32f
Source dataset
uspto-grants-2009_01
Patent number
US07473688B2

Reaction notes

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