Trimethylsilyldiazomethane → Methyl indole-6-carboxylate

HRID 1432866Notes

Reaction equation

HRID 1432866 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.[CH3:13][Si](C=[N+]=[N-])(C)C>C1COCC1.CO>[CH3:13][O:11][C:10]([C:7]1[CH:8]=[C:9]2[C:4]([CH:3]=[CH:2][NH:1]2)=[CH:5][CH:6]=1)=[O:12]

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 5952301H-indole-6-carboxylic acid

Product 1

HCID 639844Methyl indole-6-carboxylate

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 6-indole carboxylic acid (0.91 g, 5.67 mmol) in 33 mL of 2:1 THF/MeOH is added (trimethylsilyl)diazomethane (5.0 mL of a 2.0M solution in hexanes, 10.0 mmol). The mixture is stirred for 3 h and concentrated in vacuo to give the title compound (0.87 g, 4.97 mmol). The crude product is used in the next step without further purification. 1H NMR (CDCl3, 300 MHz) δ8.70 (bs, 1H), 8.20 (s, 1H), 7.82 (dd, 1H), 7.67 (d, 1H), 7.45 (m, 1H), 6.60 (m, 1H), 3.95 (s, 3H).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2cbe67bf21f540f983291d65ce98ef0e
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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