1,3-Dichloroacetone → HCID 55267106, compound

HRID 334572Notes

Reaction equation

HRID 334572 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[Cl:9][CH2:10][C:11](=O)[CH2:12]Cl>CCO>[Cl:9][CH2:10][C:11]1[N:8]=[C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][N:6]2[CH:12]=1

Participants

4

Reactant 2

HCID 107931,3-DichloroacetoneHCID 27377012-Amino-5-fluoropyridine

Product 1

HCID 55267106HCID 55267106, compoundYield 57.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

According to the general protocol described in J. Heterocyclic. Chem., 1988, 25, 129-137, to solution of 5-fluoropyridin-2-amine (1.80 g, 16 mmol) in EtOH (24 mL) was added 1,3-dichloropropan-2-one (2.03 g, 16 mmol) and the resulting mixture was stirred overnight at 80° C. The solvent was evaporated, and the residue was dissolved in a minimum volume of water. The solution was neutralized (pH=8) with saturated NaHCO3. The aqueous layer was extracted with AcOEt and the organic layer was washed with saturated NaCl. The solvent was evaporated and the crude product was purified by chromatography (prepacked 25 g silicagel column, DCM as eluent) to afford 1.7 g of 2-(chloromethyl)-6-fluoro-imidazo[1,2-a]pyridine (Yield: 57%) as a beige solid.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in a minimum volume of water
  3. extractionThe aqueous layer was extracted with AcOEt
  4. washthe organic layer was washed with saturated NaCl
  5. customThe solvent was evaporated
  6. customthe crude product was purified by chromatography (prepacked 25 g silicagel column, DCM as eluent)

Sources & evidence

ORD record
ord-64922d1408e04e9f85de29320bc46e99
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

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