Pyridine → Ethyl 2-cyano-2-(2,6-difluorobenzamido)acetate

HRID 73602

Reaction equation

HRID 73602 reaction equation
[NH2:1][CH:2]([C:8]#[N:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].N1C=CC=CC=1.[F:16][C:17]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[C:18]=1[C:19](Cl)=[O:20]>ClCCl.C(OCC)(=O)C>[C:8]([CH:2]([NH:1][C:19](=[O:20])[C:18]1[C:17]([F:16])=[CH:25][CH:24]=[CH:23][C:22]=1[F:26])[C:3]([O:5][CH2:6][CH3:7])=[O:4])#[N:9]

Participants

6

Reactant 3

HCID 1049PyridineHCID 874382,6-Difluorobenzoyl chlorideHCID 288716Ethyl 2-amino-2-cyanoacetate

Product 1

HCID 59455767Ethyl 2-cyano-2-(2,6-difluorobenzamido)acetateYield 84%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 2-amino-2-cyanoacetate (1 eq) in 6 mL of dichloromethane was added pyridine (1.5 eq) and 2,6-difluorobenzoyl chloride (1 eq) at 0° C. The reaction mixture was stirred at room temperature for 3 hours. The mixture was diluted with ethyl acetate, washed with brine, then dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The crude residue was purified by flash chromatography (EtOAc:hexanes=1:1) to give the titled compound (84%). LC/MS (m/z): 269.1 (MH+), Rt:0.69 min.

Workup

  1. washwashed with brine
  2. dry with materialdried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified by flash chromatography (EtOAc:hexanes=1:1)

Sources & evidence

ORD record
ord-72d5fc39bbfc49b5ba0f15c0aed6f4b3
Source dataset
uspto-grants-2014_09
Patent number
US08829193B2

Linked notes

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