Pyridine → N-(6-Fluoro-3-pyridinyl)cyclopropanecarboxamide

HRID 893075Notes

Reaction equation

HRID 893075 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([F:8])=[N:6][CH:7]=1.N1C=CC=CC=1.[CH:15]1([C:18](Cl)=[O:19])[CH2:17][CH2:16]1>ClCCl>[F:8][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:18]([CH:15]2[CH2:17][CH2:16]2)=[O:19])=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 77637Cyclopropanecarbonyl chlorideHCID 8194405-Amino-2-fluoropyridine

Product 1

HCID 14304481N-(6-Fluoro-3-pyridinyl)cyclopropanecarboxamideYield 72.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-amino-2-fluoropyridine (6.63 g, 0.059 mol) and pyridine (5.16 g, 0.065 mol) in dichloromethane (120 ml) was stirred at room temperature. Cyclopropane carboxylic acid chloride (6.2 g, 0.059 mol) was added dropwise to the reaction mixture at such a rate to maintain the temperature at 20°-30° C. After complete addition the reaction mixture was stirred at temperature for a further one hour, then washed with 5% sodium hydroxide (100 ml), water (100 ml) and dried over anhydrous magnesium sulphate. Removal of the solvent gave a dark brown solid which was purified by column chromatography (silica eluted with dichloromethane : tetrahydrofuran=9:1) to give N-(2-fluoro-5-pyridyl)cyclopropane carboxamide (7.7 g, 72%) as an orange brown solid m.p. 116°-117° C.

Workup

  1. temperatureto maintain the temperature at 20°-30° C
  2. additionAfter complete addition the reaction mixture
  3. washwashed with 5% sodium hydroxide (100 ml), water (100 ml)
  4. dry with materialdried over anhydrous magnesium sulphate
  5. customRemoval of the solvent
  6. customgave a dark brown solid which
  7. customwas purified by column chromatography (silica eluted with dichloromethane : tetrahydrofuran=9:1)

Sources & evidence

ORD record
ord-d2a328ae42914370b54b89d468380b30
Source dataset
uspto-grants-1992_06
Patent number
US05122529

Reaction notes

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