Ethyl 3-chloro-3-oxopropionate → HCID 86720175, compound

HRID 1770661Notes

Reaction equation

HRID 1770661 reaction equation
[NH2:1][C:2]1[C:3]([C:12](=[O:14])[CH3:13])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.Cl[C:16](=[O:23])[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]>C(Cl)Cl.O>[C:12]([C:3]1[C:2]([NH:1][C:16](=[O:23])[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:7][C:6]([C:8]([F:11])([F:9])[F:10])=[CH:5][N:4]=1)(=[O:14])[CH3:13]

Participants

5

Reactant 2

HCID 118931Ethyl 3-chloro-3-oxopropionateHCID 72214619HCID 72214619, compound

Product 1

HCID 86720175HCID 86720175, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(3-amino-5-(trifluoromethyl)pyridin-2-yl)ethanone (0.87 g, 4.26 mmol, 1 eq.) in DCM (20 ml) were added TEA (0.65 ml, 4.69 mmol, 1.1 eq.) and ethyl 3-chloro-3-oxopropanoate (0.71 ml, 5.54 mmol, 1.3 eq.) at 0° C. The reaction mixture was stirred at RT for 3 h. Then the mixture was diluted with water (50 ml) and extracted with DCM (3×80 ml). The combined organic layers were washed with water (80 ml), dried over anhydrous Na2SO4 and concentrated in vacuo to provide ethyl 3-(2-acetyl-5-(trifluoromethyl)pyridin-3-ylamino)-3-oxopropanoate (1.35 g, 4.24 mmol, 99%) which was used in subsequent reactions without further purification.

Workup

  1. extractionextracted with DCM (3×80 ml)
  2. washThe combined organic layers were washed with water (80 ml)
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-53bb05afe4494a0b8ed1aed46456091a
Source dataset
uspto-grants-2016_02
Patent number
US09248122B2

Reaction notes

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