Water → N-[6-(4-amino-2-fluorophenoxy)-3-methylimidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide

HRID 2095842Notes

Reaction equation

HRID 2095842 reaction equation
[F:1][C:2]1[CH:24]=[C:23]([N+:25]([O-])=O)[CH:22]=[CH:21][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]2[N:9]([C:11]([CH3:20])=[C:12]([NH:14][C:15]([CH:17]3[CH2:19][CH2:18]3)=[O:16])[N:13]=2)[CH:10]=1.[Cl-].[NH4+].O>C(O)C.C(OCC)(=O)C>[NH2:25][C:23]1[CH:22]=[CH:21][C:3]([O:4][C:5]2[CH:6]=[CH:7][C:8]3[N:9]([C:11]([CH3:20])=[C:12]([NH:14][C:15]([CH:17]4[CH2:19][CH2:18]4)=[O:16])[N:13]=3)[CH:10]=2)=[C:2]([F:1])[CH:24]=1

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 58158621N-[6-(2-fluoro-4-nitrophenoxy)-3-methylimidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide

Product 1

HCID 58158557N-[6-(4-amino-2-fluorophenoxy)-3-methylimidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamideYield 82%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixed solution of N-[6-(2-fluoro-4-nitrophenoxy)-3-methylimidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide (80 mg, 0.216 mmol), reduced iron (64 mg, 1.08 mmol) and ammonium chloride (116 mg, 2.16 mmol) in ethanol (2 mL)/water (0.5 mL) was stirred at 80° C. for 3 hr. The reaction mixture was diluted with ethyl acetate and filtered through celite. Water was added to the filtrate, and the mixture was extracted 3 times 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 to give the title compound (60 mg, 82%) as a slightly yellow solid.

Workup

  1. filtrationfiltered through celite
  2. additionWater was added to the filtrate
  3. extractionthe mixture was extracted 3 times with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-25ec52f32e734d4ab9442ebfd89b05d0
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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