Ethyl 4-chloroacetoacetate → HCID 86683109, compound

HRID 920890Notes

Reaction equation

HRID 920890 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1.Cl[CH2:10][C:11](=O)[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][N:5]2[CH:10]=[C:11]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:8]=[C:4]2[CH:3]=1

Participants

4

Reactant 2

HCID 69484Ethyl 4-chloroacetoacetateHCID 183278082-Amino-4-fluoropyridine

Product 1

HCID 86683109HCID 86683109, compoundYield 17.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-fluoropyridin-2-amine (1.0 g, 8.92 mmol) and ethyl 4-chloro-3-oxobutanoate (1.46 mL, 10.7 mmol) in THF (20 mL) was stirred at about reflux overnight. The residue was concentrated and was chromatographed on the C18 ISCO Combiflash system using the following gradient: A: Water (0.1% NH4HCO3); B: Methanol; 10% B to 60% B over 20 min to give 350 mg product as brown oil (350 mg, yield: 17.6%).

Workup

  1. temperatureabout reflux overnight
  2. concentrationThe residue was concentrated
  3. customwas chromatographed on the C18 ISCO Combiflash system

Sources & evidence

ORD record
ord-6ebfe3e6652242c38d1910421a6138aa
Source dataset
uspto-grants-2016_03
Patent number
US09273068B2

Reaction notes

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