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

HRID 2095871Notes

Reaction equation

HRID 2095871 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([NH:11][C:12]([CH:14]3[CH2:16][CH2:15]3)=[O:13])[N:10]=2)[CH:7]=1.F[C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][C:19]=1[F:27].C(=O)([O-])[O-].[Cs+].[Cs+].O>CS(C)=O>[F:27][C:19]1[CH:20]=[C:21]([N+:24]([O-:26])=[O:25])[CH:22]=[CH:23][C:18]=1[O:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([NH:11][C:12]([CH:14]3[CH2:15][CH2:16]3)=[O:13])[N:10]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 1230531,2-Difluoro-4-nitrobenzeneHCID 58158532N-(6-Hydroxyimidazo[1,2-A]pyridin-2-YL)cyclopropanecarboxamide

Product 1

HCID 58158487N-[6-(2-fluoro-4-nitrophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamideYield 95%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of N-(6-hydroxyimidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide (30 g, 138 mmol) and 1,2-difluoro-4-nitrobenzene (24.2 g, 152 mmol) in dimethyl sulfoxide (180 mL) was added cesium carbonate (58.5 g, 180 mmol), and the mixture was stirred at room temperature for 5 hr under an argon atmosphere. Water (1080 mL) was added to the reaction mixture, and the mixture was stirred for 20 min. The precipitate was collected by filtration and washed with water and ethyl acetate. After air drying for one day, the mixture was dried under reduced pressure at 100° C. for 5 hr to give the title compound (46.5 g, 95%) as a yellow solid.

Workup

  1. stirringthe mixture was stirred for 20 min
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water and ethyl acetate
  4. customAfter air drying for one day
  5. customthe mixture was dried under reduced pressure at 100° C. for 5 hr

Sources & evidence

ORD record
ord-53ded839a9a243689c1d45bfb5f3780d
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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