Tert-Butyl nitrite → HCID 86692640, compound

HRID 1748689Notes

Reaction equation

HRID 1748689 reaction equation
N(OC(C)(C)C)=O.[CH2:8]([O:10][C:11]([C:13]1[CH:14]=[N:15][N:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][N:20]=2)[C:17]=1N)=[O:12])[CH3:9].[Cl:29]N1C(=O)CCC1=O>ClCCl>[CH2:8]([O:10][C:11]([C:13]1[CH:14]=[N:15][N:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][N:20]=2)[C:17]=1[Cl:29])=[O:12])[CH3:9]

Participants

5

Reactant 3

HCID 10906Tert-Butyl nitriteHCID 31398ChlorosuccinimideHCID 722162Ethyl 5-amino-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxylate

Product 1

HCID 86692640HCID 86692640, compoundYield 43.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl nitrite (154 mg) was added slowly dropwise to a solution of 5-amino-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester (300 mg) and N-chlorosuccinimide (200 mg) in dichloromethane (10 ml) and stirred at room temperature for three hours. The reaction solution was concentrated while keeping not dried up, and the residue was purified with silica gel chromatography (ethyl acetate/n-hexane) to give 5-chloro-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester (140 mg) as a white solid.

Workup

  1. concentrationThe reaction solution was concentrated
  2. customwhile keeping not dried up
  3. customthe residue was purified with silica gel chromatography (ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-17d45f2bf9e4487ca01c558d3046cc21
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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