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

HRID 629163Notes

Reaction equation

[CH2:1]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]([CH:15]=[O:16])=[CH:9]2)[CH2:2][CH:3]([CH3:5])[CH3:4].CI.[C:19](=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:1]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH3:19])[C:10]([CH:15]=[O:16])=[CH:9]2)[CH2:2][CH:3]([CH3:5])[CH3:4]

Participants

Conditions

Temperature: 150 °C

Procedure

To a solution of 5-isopentyl-1H-indole-2-carbaldehyde (100 mg, 0.46 mmol) and methyl iodide (71 mg, 0.50 mmol) in 0.93 mL dimethylformamide was added potassium carbonate (71 mg, 0.51 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-isopentyl-1-methyl-1H-indole-2-carbaldehyde (16 mg, 15%).

Workup

filtrationSolids were filtered
concentrationthe liquor concentrated

Sources & evidence

ORD record: ord-77b412ea565e44de8971bece1e8e4a3c
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09315495B2

Reaction notes

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