Ethyl 2-chloroacetoacetate → HCID 86717940, compound

HRID 2275868Notes

Reaction equation

HRID 2275868 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:3]=1[CH2:4][O:5][C:6]1[C:7]([NH2:13])=[N:8][CH:9]=[CH:10][C:11]=1[F:12].Cl[CH:20]([C:26]([CH3:28])=O)[C:21]([O:23][CH2:24][CH3:25])=[O:22]>C(O)C>[F:1][C:2]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:26]([CH3:28])[N:13]=2)[CH:9]=[CH:10][C:11]=1[F:12]

Participants

4

Reactant 2

HCID 11858Ethyl 2-chloroacetoacetateHCID 86717939HCID 86717939, compound

Product 1

HCID 86717940HCID 86717940, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under argon, 500 mg (1.97 mmol) of 3-[(2,6-difluorobenzyl)oxy]-4-fluoropyridine-2-amine Example 268A were initially charged in 10 ml of ethanol, 500 mg of powdered molecular sieve 4A and 3.24 g (19.67 mmol) of ethyl 2-chloroacetoacetate were added and the mixture was then heated at reflux for 48 h. All volatile components were evaporated at 85° C. under reduced pressure. The crude product was purified by silica gel chromatography (mobile phase: cyclohexane/ethyl acetate=9/1 isocratic). This gave 368 mg (39% of theory; purity about 76%) of the title compound.

Workup

  1. temperaturethe mixture was then heated
  2. temperatureat reflux for 48 h
  3. customAll volatile components were evaporated at 85° C. under reduced pressure
  4. customThe crude product was purified by silica gel chromatography (mobile phase: cyclohexane/ethyl acetate=9/1 isocratic)

Sources & evidence

ORD record
ord-bc5e1c9fb08c4764b6e8495a758118ce
Source dataset
uspto-grants-2015_09
Patent number
US09126998B2

Reaction notes

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