Pyridine → HCID 58724547, compound

HRID 1393044Notes

Reaction equation

HRID 1393044 reaction equation
[CH3:1][N:2]1[C:6]([N:7]2[CH:11]=[CH:10][CH:9]=[CH:8]2)=[C:5]([C:12]([OH:14])=O)[CH:4]=[N:3]1.N1C=CC=CC=1.N1C(F)=NC(F)=NC=1[F:23]>ClCCl>[CH3:1][N:2]1[C:6]([N:7]2[CH:11]=[CH:10][CH:9]=[CH:8]2)=[C:5]([C:12]([F:23])=[O:14])[CH:4]=[N:3]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 12664Cyanuric fluorideHCID 155002461-Methyl-5-(1H-pyrrol-1-yl)-1H-pyrazole-4-carboxylic acid

Product 1

HCID 58724547HCID 58724547, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 1-methyl-5-pyrrol-1-yl-1H-pyrazole-4-carboxylic acid (7.65 g, 40 mmol) in dry dichloromethane (150 mL) and pyridine (3.2 mL, 40 mmol) under a nitrogen atmosphere was added cyanuric fluoride (5.4 g, 40 mmol) at 0° C. The reaction mixture was stirred for two hours during which time the reaction temperature was allowed to rise to room temperature. Crushed ice was then added along with additional dichloromethane. The organic layer was separated and the aqueous layer was extracted twice with dichloromethane. Concentration of the combined organic layers under reduced pressure gave 1-methyl-5-pyrrol-1-yl-1H-pyrazole-4-carbonyl fluoride which was used in the next step without further purification.

Workup

  1. customto rise to room temperature
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted twice with dichloromethane

Sources & evidence

ORD record
ord-dde0e4045b7648f1953776d2217ab9d5
Source dataset
uspto-grants-2008_03
Patent number
US07345058B2

Reaction notes

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