Methyl iodide → HCID 15224434, compound

HRID 2119883Notes

Reaction equation

[CH3:1][CH:2]([OH:21])[CH2:3][C:4]1[N:5]([CH2:17][CH:18]([CH3:20])[CH3:19])[C:6]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:16]=1.[H-].[Na+].[CH3:24]I>CN(C)C=O>[CH3:24][O:21][CH:2]([CH3:1])[CH2:3][C:4]1[N:5]([CH2:17][CH:18]([CH3:20])[CH3:19])[C:6]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:16]=1

Participants

Conditions

Temperature: 0 °C

Procedure

α-Methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline-2-ethanol (6.5 g, 23 mmol, Example 74) was dissolved in N,N-dimethylformamide (50 mL) then cooled to 0° C. Sodium hydride (0.8 g, 25 mmol), 80% dispersion in mineral oil) was added and the resulting mixture was stirred at 0° C. for about 1 hour. Methyl iodide (2.2 mL, 34 mmol) was added and the resulting mixture was stirred at 0° C. for about 1 hour and then allowed to warm to room temperature. The reaction was quenched with water and then diluted with ethyl acetate. The organic layer was separated, washed several times with water, dried over magnesium sulfate then concentrated under vacuum. The resulting residue was purified by silica gel chromatography using 2-5% methanol in methylene chloride to give about 3 g of the desired product. The structure was confirmed by nuclear magnetic resonance spectroscopy.

Workup

stirringthe resulting mixture was stirred at 0° C. for about 1 hour
temperatureto warm to room temperature
customThe reaction was quenched with water
additiondiluted with ethyl acetate
customThe organic layer was separated
washwashed several times with water
dry with materialdried over magnesium sulfate
concentrationthen concentrated under vacuum
customThe resulting residue was purified by silica gel chromatography

Sources & evidence

ORD record: ord-8b864af91203426597a397a61bf7d3d1
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06686472B2

Reaction notes

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