Chlorine → HCID 22672588, compound

HRID 1006681Notes

Reaction equation

HRID 1006681 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 was 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-de8098c32fbb4f47998baf0ad9cef593
Source dataset
uspto-grants-2004_09
Patent number
US06790960B2

Reaction notes

Loading…