1,1'-Carbonyldiimidazole → 5-(2-Fluorocyclopropyl)-3-(4-methyl-3-nitrophenyl)-1,2,4-oxadiazole

HRID 1497899Notes

Reaction equation

[F:1][C@@H:2]1[CH2:4][C@H:3]1[C:5]([OH:7])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.O[N:21]=[C:22]([NH2:33])[C:23]1[CH:28]=[CH:27][C:26]([CH3:29])=[C:25]([N+:30]([O-:32])=[O:31])[CH:24]=1>CN1C(=O)CCC1>[F:1][CH:2]1[CH2:4][CH:3]1[C:5]1[O:7][N:33]=[C:22]([C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[C:25]([N+:30]([O-:32])=[O:31])[CH:24]=2)[N:21]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a stirring solution of trans-2-Fluoro-cyclopropanecarboxylic acid (0.38 g, 3.68 mmol) in anhydrous NMP (12 mL) was added 1,1′-carbonyldiimidazole (CDI) (0.59 g, 3.68 mmol). The reaction was stirred for 3 minutes. N′-hydroxy-4-methyl-3-nitrobenzimidamide (27) (0.72 g, 3.68 mmol) was added and the reaction was stirred for minutes then heated in the microwave at 120° C. for 15 minutes. The crude product was extracted with ethyl acetate. The organic layer was washed with water, brine and dried over anhydrous sodium sulfate. The solvent was concentrated and the crude product was purified on silica gel using ethyl acetate and hexane to yield 5-(2-fluorocyclopropyl)-3-(4-methyl-3-nitrophenyl)-1,2,4-oxadiazole (129). MS m/z 264.1 (M+1)+.

Workup

stirringthe reaction was stirred for minutes
extractionThe crude product was extracted with ethyl acetate
washThe organic layer was washed with water, brine
dry with materialdried over anhydrous sodium sulfate
concentrationThe solvent was concentrated
customthe crude product was purified on silica gel

Sources & evidence

ORD record: ord-b01aa1f4299d4e5c921b463be0f6a826
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199981B2

Reaction notes

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