Chlorine → HCID 22672588, compound

HRID 1369577Notes

Reaction equation

HRID 1369577 reaction equation
[CH3:1][C:2]1[CH:19]=[C:18]([F:20])[CH:17]=[C:16]([CH3:21])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([CH:12]=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1.[Cl:22]Cl>C(O)(=O)C>[CH3:21][C:16]1[CH:17]=[C:18]([F:20])[CH:19]=[C:2]([CH3:1])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:12]([Cl:22])=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 24526ChlorineHCID 22672633HCID 22672633, compound

Product 1

HCID 22672588HCID 22672588, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 8-(2,6-dimethyl-4-fluorobenzyloxy)-2-methylimidazo[1,2-a]pyridine (0.6 g, 2.1 mmol) in acetic acid (13 ml) was added dropwise 1.1 M Cl2 in acetic acid (2.2 ml, 2.43 mmol). The reaction mixture was stirred for 2 h. at room temperature and the solvent was evaporated under reduced pressure. The residue weas solved in methylene chloride and was washed with water. The organic layer was separated, dried and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using methylene chloride:ethyl acetate (100:4) as eluent. Treating the residue with diethyl ether and filtration gave 0.3 g (45%) of the title compound.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. washwas washed with water
  3. customThe organic layer was separated
  4. customdried
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel
  7. additionTreating the residue
  8. filtrationwith diethyl ether and filtration

Sources & evidence

ORD record
ord-0174a5568cdb4aa7be329943f7724815
Source dataset
uspto-grants-2003_06
Patent number
US06579884B1

Reaction notes

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