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

HRID 1807840Notes

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-80db762bcda749ac84aaaf5365c39d6a
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08357688B2

Reaction notes

Loading…