Cesium carbonate → tert-butyl 2-{[2-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]oxy}ethylcarbamate

HRID 540824Notes

Reaction equation

I[CH2:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].[CH3:12][C:13]1[N:14]([CH2:27][CH:28]([CH3:30])[CH3:29])[C:15]2[C:24]3[CH:23]=[CH:22][C:21]([OH:25])=[CH:20][C:19]=3[N:18]=[CH:17][C:16]=2[N:26]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH3:12][C:13]1[N:14]([CH2:27][CH:28]([CH3:30])[CH3:29])[C:15]2[C:24]3[CH:23]=[CH:22][C:21]([O:25][CH2:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[CH:20][C:19]=3[N:18]=[CH:17][C:16]=2[N:26]=1

Participants

Conditions

Temperature: 60 °C

Procedure

tert-Butyl 2-iodoethylcarbamate (2.55 g, 9.41 mmol), prepared as described in Parts J and K of Example 2, was added to a mixture of 2-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-ol (2.00 g, 7.83 mmol) and cesium carbonate (3.83 g, 11.7 mmol) in DMF (30 mL), and the reaction was heated at 60° C. for four hours. The solvent was removed under reduced pressure, and the resulting solid was triturated with water and isolated by filtration to yield 2.57 g of tert-butyl 2-{[2-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]oxy}ethylcarbamate as a light-brown solid.

Workup

customThe solvent was removed under reduced pressure
customthe resulting solid was triturated with water
customisolated by filtration

Sources & evidence

ORD record: ord-21f4bf8268ec432293c564a7b44bcc03
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871782B2

Reaction notes

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