Triethylamine → HCID 22632890, compound

HRID 2416818Notes

Reaction equation

HRID 2416818 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][C:5]([F:13])=[C:4](Cl)[N:3]=1.[CH2:15]([N:17](CC)[CH2:18][CH3:19])[CH3:16].N1CCCC1>C(#N)C>[Cl:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][C:5]([F:13])=[C:4]([N:17]2[CH2:18][CH2:19][CH2:16][CH2:15]2)[N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 13210747Ethyl 2,6-dichloro-5-fluoropyridine-3-carboxylate

Product 1

HCID 22632890HCID 22632890, compoundYield 72.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of ethyl 2,6-dichloro-5-fluoro-3-pyridinecarboxylate (3.00 g, 12.6 mmol: J. Med. Chem., 1986;29:2363) and triethylamine (2.63 mL, 18.90 mmol) in acetonitrile (15 mL) was added pyrrolidine (1.05 mL, 12.6 mmol) dropwise. After being stirred at 60° C. for 1 hour, the reaction mixture was evaporated, and the residue was dissolved in dichloromethane, washed with water, and dried over anhydrous sodium sulfate. The residue was purified on a silica gel column using hexane/dichloromethane (7:3) as eluent giving 2.5 g of the title compound as a solid, mp 95° C.

Workup

  1. customthe reaction mixture was evaporated
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-84ebd1656072434faf88d9dc9d63e775
Source dataset
uspto-grants-2004_11
Patent number
US06825199B2

Reaction notes

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