Dimethylformamide → Ethyl 1-(methoxymethyl)-7-nitro-5-(trifluoromethoxy)-1H-indole-2-carboxylate

HRID 1851381Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]([O:18][C:19]([F:22])([F:21])[F:20])[CH:7]=[C:8]2[C:12]=1[NH:11][C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:9]2)([O-:3])=[O:2].[H-].[Na+].CN(C)C=O.[CH3:30][O:31][CH2:32]Cl>O1CCCC1.C(OCC)(=O)C>[CH3:30][O:31][CH2:32][N:11]1[C:12]2[C:8](=[CH:7][C:6]([O:18][C:19]([F:22])([F:20])[F:21])=[CH:5][C:4]=2[N+:1]([O-:3])=[O:2])[CH:9]=[C:10]1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

Conditions

Temperature: 4 °C

Procedure

A mixture of ethyl 7-nitro-5-(trifluoromethoxy)-1H-indole-2-carboxylate (1.19 g), 60% sodium hydride (0.18 g) and N,N-dimethylformamide (20 mL) was stirred at 4° C. for 20 min. A solution (5 mL) of chloromethyl methyl ether (0.33 mL) in tetrahydrofuran was added dropwise. After stirring at 4° C. for 3 hr, the reaction solution was diluted with ethyl acetate, washed with aqueous citric acid solution, water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=5:95-20:80) to give the title compound (1.0 g, yield 74%) as pale-yellow prism crystals.

Workup

stirringAfter stirring at 4° C. for 3 hr
washwashed with aqueous citric acid solution, water and saturated brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-ae052c4d4623480a8860a0db8fb5bd7a
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957070B2

Reaction notes

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