Ethyl 4,4,4-trifluoroacetoacetate → N-[4-chloro-2-fluoro-5-{2-(methoxycarbonyl)methoxy-3-pyridyloxy}phenyl]tri fluoroacetoacetamide

HRID 493948Notes

Reaction equation

HRID 493948 reaction equation
[Cl:1][C:2]1[C:8]([O:9][C:10]2[C:11]([O:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[N:12][CH:13]=[CH:14][CH:15]=2)=[CH:7][C:5]([NH2:6])=[C:4]([F:22])[CH:3]=1.[F:23][C:24]([F:34])([F:33])[C:25](=[O:32])[CH2:26][C:27](OCC)=[O:28]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:8]([O:9][C:10]2[C:11]([O:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[N:12][CH:13]=[CH:14][CH:15]=2)=[CH:7][C:5]([NH:6][C:27](=[O:28])[CH2:26][C:25]([C:24]([F:34])([F:33])[F:23])=[O:32])=[C:4]([F:22])[CH:3]=1

Participants

4

Reactant 2

HCID 67793Ethyl 4,4,4-trifluoroacetoacetateHCID 219335774-Chloro-2-fluoro-5-{2-(methoxycarbonyl)methoxy-3-pyridyloxy}aniline

Product 1

HCID 86593477N-[4-chloro-2-fluoro-5-{2-(methoxycarbonyl)methoxy-3-pyridyloxy}phenyl]tri fluoroacetoacetamideYield 100.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 0.5 g of 4-chloro-2-fluoro-5-{2-(methoxycarbonyl)methoxy-3-pyridyloxy}aniline, 0.28 g of ethyl trifluoroacetoacetate, and 10 ml of toluene was azeotropically distilled for 3 hours, while passing through molecular sieves 5A to remove ethanol. After cooling, the reaction mixture was concentrated to give 0.71 g of N-[4-chloro-2-fluoro-5-{2-(methoxycarbonyl)methoxy-3-pyridyloxy}phenyl]trifluoroacetoacetamide.

Workup

  1. distillationwas azeotropically distilled for 3 hours
  2. customto remove ethanol
  3. temperatureAfter cooling
  4. concentrationthe reaction mixture was concentrated

Sources & evidence

ORD record
ord-285ea85398d640aeb18e1105c2fd8e9d
Source dataset
uspto-grants-2009_05
Patent number
US07538072B2

Reaction notes

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