Methyl 2,2-Difluoro-3-methoxypropionate → N'-(5-bromopyridin-2-yl)-2,2-difluoro-3-methoxypropanehydrazide

HRID 406442Notes

Reaction equation

HRID 406442 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH2:9])=[N:6][CH:7]=1.[F:10][C:11]([F:19])([CH2:16][O:17][CH3:18])[C:12](OC)=[O:13]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH:9][C:12](=[O:13])[C:11]([F:19])([F:10])[CH2:16][O:17][CH3:18])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 2769543Methyl 2,2-Difluoro-3-methoxypropionateHCID 115356995-Bromo-2-hydrazinopyridine

Product 1

HCID 66849873N'-(5-bromopyridin-2-yl)-2,2-difluoro-3-methoxypropanehydrazide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

(5-bromo-2-hydrazinylpyridine (1.83 g, 9.73 mmol) and methyl 2,2-difluoro-3-methoxypropanoate (1.00 g, 6.49 mmol) were refluxed in toluene (35 mL) overnight. The reaction mixture was concentrated and purified by chromatography (EtOAc: hexanes=1:4) to give N′-(5-bromopyridin-2-yl)-2,2-difluoro-3-methoxypropanehydrazide.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by chromatography (EtOAc: hexanes=1:4)

Sources & evidence

ORD record
ord-2a7604a821444d9ba2a45a869634ef88
Source dataset
uspto-grants-2014_06
Patent number
US08754103B2

Reaction notes

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