Diazomethane → Methyl indole-6-carboxylate

HRID 1769884Notes

Reaction equation

HRID 1769884 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([OH:12])=[O:11])[CH:8]=2)[CH:3]=[CH:2]1.[N+](=[CH2:15])=[N-]>O1CCCC1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([O:12][CH3:15])=[O:11])[CH:8]=2)[CH:3]=[CH:2]1

Participants

4

Reactant 2

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

Product 1

HCID 639844Methyl indole-6-carboxylateYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of indole-6-carboxylic acid (2.0 g, 12.4 mmol), prepared as described in step 1, in tetrahydrofuran (20 mL) at 0° C. was added excess diazomethane (0.30M solution in ether). After 10 min the solution was warmed to room temperature and nitrogen was bubbled through the solution for 30 min. The solution was concentrated in vacuo and the residue purified by flash chromatography (SiO2, 85:15 hexane:ethyl acetate) to afford methyl indole-6-carboxylate (2.1 g, 98 %) as a white solid.

Workup

  1. customnitrogen was bubbled through the solution for 30 min
  2. concentrationThe solution was concentrated in vacuo
  3. customthe residue purified by flash chromatography (SiO2, 85:15 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-b79f1181307d4721bb2b9629b484e691
Source dataset
uspto-grants-1995_01
Patent number
US05382670

Reaction notes

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