Ethyl 2-chloroacetoacetate → HCID 86718218, compound

HRID 1844190Notes

Reaction equation

HRID 1844190 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:9][CH2:10][C:11]2[C:16]([F:17])=[CH:15][CH:14]=[CH:13][N:12]=2)[C:5]([NH2:8])=[N:6][CH:7]=1.Cl[CH:19]([C:25](=O)[CH3:26])[C:20]([O:22][CH2:23][CH3:24])=[O:21].FC1C=NC=C(F)C=1C=O>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([O:9][CH2:10][C:11]2[C:16]([F:17])=[CH:15][CH:14]=[CH:13][N:12]=2)[C:5]2[N:6]([C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:25]([CH3:26])[N:8]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 11858Ethyl 2-chloroacetoacetateHCID 116511703,5-Difluoropyridine-4-carbaldehydeHCID 86718216HCID 86718216, compound

Product 1

HCID 86718218HCID 86718218, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3.00 g (11.83 mmol) of 5-chloro-3-[(3-fluoropyridin-2-yl)methoxy]pyridine-2-amine from Example 127A and 9.73 g (59.13 mmol) of ethyl 2-chloro-3-oxobutanoate were dissolved in 72 ml of ethanol and, together with 4.5 g of 3 A molecular sieve, stirred under reflux for 6 days. The mixture was cooled and filtered and the filtrate was concentrated under reduced pressure. The residue obtained was purified by silica gel chromatography (mobile phase: cyclohexane/ethyl acetate gradient=4/1 to 2/1). This gave 2.0 g (46% of theory) of the target compound.

Workup

  1. temperatureunder reflux for 6 days
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue obtained
  6. customwas purified by silica gel chromatography (mobile phase: cyclohexane/ethyl acetate gradient=4/1 to 2/1)

Sources & evidence

ORD record
ord-2d417181ec264285ab7b160ccd5ca2d3
Source dataset
uspto-grants-2015_02
Patent number
US08946215B2

Reaction notes

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