Methyl iodide → 1-methyl-1H-indole-5-carbaldehyde

HRID 1866236Notes

Reaction equation

HRID 1866236 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](C(N)=O)=[C:6]2SC1C=CC=CC=1)=[O:2].[CH3:22]I>CO.C(Cl)Cl>[CH:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:22])[CH:7]=[CH:6]2)=[O:2]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 76850762HCID 76850762, compound

Product 1

HCID 75375341-methyl-1H-indole-5-carbaldehyde

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Treat 5-formyl-3-phenylsulfanyl-1H-indole-2-carboxylic acid amide 13 (m=0, R3=Ph; 400 mg, 1.35 mmol) with MeI (101 μl) as described in General Procedure XIV to provide the 5-formyl-1-methylindole the title compound 14 (280 mg, 67%), Rf (5% MeOH/CH2Cl2)=0.75.

Sources & evidence

ORD record
ord-bdcc0ee743f347458849c26cea8598ab
Source dataset
uspto-grants-2009_12
Patent number
US07629376B2

Reaction notes

Loading…