Acetonitrile → methyl 4-(2-cyclopentyl-1H-imidazol-1-yl)-2-methyl-5-nitrobenzoate

HRID 1189452Notes

Reaction equation

F[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH3:15])[CH:3]=1.FC1C=CC(C(OC)=O)=C(C)C=1[N+]([O-])=O.[CH:31]1([C:36]2[NH:37][CH:38]=[CH:39][N:40]=2)[CH2:35][CH2:34][CH2:33][CH2:32]1.C(#N)C>C(OCC)(=O)C.O.C(N(CC)CC)C>[CH:31]1([C:36]2[N:37]([C:2]3[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH3:15])[CH:3]=3)[CH:38]=[CH:39][N:40]=2)[CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

Conditions

Temperature: 70 °C

Procedure

To 2.74 g of a mixture of methyl 4-fluoro-2-methyl-5-nitrobenzoate and methyl 4-fluoro-2-methyl-3-nitrobenzoate, 1.75 g of 2-cyclopentyl-1H-imidazole, and 17.5 mL of acetonitrile, was added 4.9 mL of triethylamine, followed by stirring at 70° C. for 7 hours. To the reaction mixture were added water and ethyl acetate, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and then dried over anhydrous magnesium sulfate, and then solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (normal hexane/ethyl acetate) to obtain 2.12 g of methyl 4-(2-cyclopentyl-1H-imidazol-1-yl)-2-methyl-5-nitrobenzoate.

Workup

extractionfollowed by extraction with ethyl acetate
washThe organic layer was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
customsolvent was evaporated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (normal hexane/ethyl acetate)

Sources & evidence

ORD record: ord-3e1235f3dad24a468de08e7ea9b791e2
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08674096B2

Reaction notes

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