Hydrochloric Acid → N-[3-fluoro-6-(2-fluoro-4-nitrophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide

HRID 2095859Notes

Reaction equation

HRID 2095859 reaction equation
[F:1][C:2]1[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[CH:21]=[CH:20][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]2[N:9]([CH:11]=[C:12]([NH:14][C:15]([CH:17]3[CH2:19][CH2:18]3)=[O:16])[N:13]=2)[CH:10]=1.O1CCCC1.OS(C(F)(F)[F:37])(=O)=O.FN1C(Cl)=CC=CC1Cl.Cl>C(#N)C.C(OCC)(=O)C>[F:37][C:11]1[N:9]2[CH:10]=[C:5]([O:4][C:3]3[CH:20]=[CH:21][C:22]([N+:24]([O-:26])=[O:25])=[CH:23][C:2]=3[F:1])[CH:6]=[CH:7][C:8]2=[N:13][C:12]=1[NH:14][C:15]([CH:17]1[CH2:19][CH2:18]1)=[O:16]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2×HCID 58158487N-[6-(2-fluoro-4-nitrophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamideHCID 866513971-Fluoro-2,6-dichloropyridine triflate

Product 1

HCID 58158450N-[3-fluoro-6-(2-fluoro-4-nitrophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamideYield 12%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-[6-(2-fluoro-4-nitrophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide (121.6 mg, 0.341 mmol) in acetonitrile (0.5 mL)/tetrahydrofuran (0.5 mL) was added 1-fluoro-2,6-dichloropyridine triflate (129 mg, 0.409 mmol), and the mixture was stirred at room temperature for 2 hr. Tetrahydrofuran, ethyl acetate and 1N hydrochloric acid were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (NH silica gel, ethyl acetate/hexane=1/2→1/1) to give the title compound (15.2 mg, 12%) as a white solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (NH silica gel, ethyl acetate/hexane=1/2→1/1)

Sources & evidence

ORD record
ord-becc1dc3cae245c3926562669af8fd1c
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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