Methyl iodide → 5-butyl-1-methyl-1H-indole-2-carbaldehyde

HRID 629161Notes

Reaction equation

[CH2:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([CH:14]=[O:15])=[CH:8]2)[CH2:2][CH2:3][CH3:4].CI.[C:18](=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH3:18])[C:9]([CH:14]=[O:15])=[CH:8]2)[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 150 °C

Procedure

To a solution of 5-butyl-1H-indole-2-carbaldehyde (75 mg, 0.37 mmol) and methyl iodide (57 mg, 0.40 mmol) in 0.75 mL dimethylformamide was added potassium carbonate (57 mg, 0.41 mmol). The resulting suspension was stirred vigorously at 150° C. in a sealed vial under argon for 1 h. Solids were filtered and the liquor concentrated before being subjected to chromatography on silica gel (40% ethyl acetate in hexanes) to give 5-butyl-1-methyl-1H-indole-2-carbaldehyde (15 mg, 18%).

Workup

filtrationSolids were filtered
concentrationthe liquor concentrated

Sources & evidence

ORD record: ord-fd48127568a9497fb79d2c32dfbb8751
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09315495B2

Reaction notes

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