Pyridine → 6-Chloro-2-(ethylamino)pyridine-3-carbonyl fluoride

HRID 2207305Notes

Reaction equation

HRID 2207305 reaction equation
N1C=CC=CC=1.[F:7]N1N=C(F)C=C(F)N1.[Cl:16][C:17]1[CH:25]=[CH:24][C:20]([C:21](O)=[O:22])=[C:19]([NH:26][CH2:27][CH3:28])[N:18]=1>ClCCl>[Cl:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([F:7])=[O:22])=[C:19]([NH:26][CH2:27][CH3:28])[N:18]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 216944332,4,6-Trifluoro-1,2,3-triazineHCID 633764796-Chloro-2-(ethylamino)nicotinic acid

Product 1

HCID 867145746-Chloro-2-(ethylamino)pyridine-3-carbonyl fluorideYield 99.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2 ml (24.8 mmol) of pyridine and 4.2 ml (49.8 mmol) of 2,4,6-trifluorotriazine were added to a suspension of 5.0 g (24.8 mmol) of 6-chloro-2-ethylamino-nicotinic acid in 125 ml of dichloromethane. The mixture was stirred for 3 hours at ambient temperature and then filtered. The solid was rinsed with 50 ml of dichloromethane and the filtrate was washed twice with 60 ml of ice-cold water. The organic phase was dried over Na2SO4 and the solvent was evaporated off under reduced pressure. 5.01 g of product were obtained in the form of an orange oil which was used without further purification.

Workup

  1. filtrationfiltered
  2. washThe solid was rinsed with 50 ml of dichloromethane
  3. washthe filtrate was washed twice with 60 ml of ice-cold water
  4. dry with materialThe organic phase was dried over Na2SO4
  5. customthe solvent was evaporated off under reduced pressure

Sources & evidence

ORD record
ord-892b107875144d8fb9d2bc4c30046293
Source dataset
uspto-grants-2016_06
Patent number
US09376432B2

Reaction notes

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