Trimethylsilyldiazomethane → HCID 68283534, compound

HRID 1527237Notes

Reaction equation

HRID 1527237 reaction equation
[C:1]([C:4]1[C:12]2[C:7](=[CH:8][C:9]([CH2:13][C:14]([OH:16])=[O:15])=[CH:10][CH:11]=2)[NH:6][CH:5]=1)(=[O:3])[CH3:2].[CH3:17][Si](C=[N+]=[N-])(C)C>CO>[CH3:17][O:15][C:14](=[O:16])[CH2:13][C:9]1[CH:8]=[C:7]2[C:12]([C:4]([C:1](=[O:3])[CH3:2])=[CH:5][NH:6]2)=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 68284032HCID 68284032, compound

Product 1

HCID 68283534HCID 68283534, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of (3-acetyl-1H-indol-6-yl)-acetic acid [39689-58-2] (500 mg, 2.85 mmol) in MeOH (14 mL), cooled to at 0° C., was added (trimethylsilyl)diazomethane (2M solution in Et2O; 6.00 mL, 12.0 mmol). After stirring at RT for 30 min, the reaction mixture was concentrated in vacuo to afford the title compound as a yellow wax. MS: 190 [M+H]+; tR (HPLC conditions k): 3.20 min. The material thus obtained was used directly in the next step without further purification.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-50144c9ef4f642e5b7862aacb171a2ee
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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