Cesium carbonate → N-[6-(3-chloro-4-nitrophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide

HRID 2095848Notes

Reaction equation

HRID 2095848 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])=[C:20]([Cl:27])[CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[Cl:27][C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][C:21]=1[N+:24]([O-:26])=[O:25])[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

5

Reactant 3

HCID 10796Cesium carbonateHCID 750172-Chloro-4-fluoro-1-nitrobenzeneHCID 58158532N-(6-Hydroxyimidazo[1,2-A]pyridin-2-YL)cyclopropanecarboxamide

Product 1

HCID 58158527N-[6-(3-chloro-4-nitrophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamideYield 111.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Using N-(6-hydroxyimidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide (200 mg, 0.92 mmol), 4-fluoro-2-chloro-1-nitrobenzene (315 mg, 1.79 mmol), dimethyl sulfoxide (4 mL) and cesium carbonate (675 mg, 2.07 mmol), and in the same manner as in Reference Example 101, the title compound (382 mg, 74%) was obtained as a yellow solid.

Sources & evidence

ORD record
ord-6bc485a386b1412b8d5315656160ce23
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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