Methanol → HCID 10838214, compound

HRID 1900001Notes

Reaction equation

HRID 1900001 reaction equation
[Br:1][C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[C:10]([O:11][CH2:12][C:13]3[C:18]([Cl:19])=[CH:17][CH:16]=[C:15]([N:20]([C:22](=[O:28])[CH2:23][O:24]C(=O)C)[CH3:21])[C:14]=3[Cl:29])[C:5]2=[N:4][C:3]=1[CH3:30].C(=O)([O-])[O-].[K+].[K+].CO>O1CCCC1>[Br:1][C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[C:10]([O:11][CH2:12][C:13]3[C:18]([Cl:19])=[CH:17][CH:16]=[C:15]([N:20]([C:22](=[O:28])[CH2:23][OH:24])[CH3:21])[C:14]=3[Cl:29])[C:5]2=[N:4][C:3]=1[CH3:30]

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 10553878HCID 10553878, compound

Product 1

HCID 10838214HCID 10838214, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-bromo-8-[3-(N-acetoxyacetyl-N-methylamino)-2,6-dichlorobenzyloxy]-2-methylimidazo[1,2-a]pyridine (1.42 g), potassium carbonate (761 mg), methanol (7 ml) and tetrahydrofuran (7 ml) was stirred at ambient temperature for 1 hour. The mixture was partitioned between dichloromethane and water. The aqueous layer was extracted with dichloromethane twice. The combined organic layers were washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was crystallized from ethanol to give 3-bromo-8-[2,6-dichloro-3-(N-glycoloyl-N-methylamino)benzyloxy]-2-methylimidazo[1,2-a]pyridine (1.16 g) as crystals.

Workup

  1. customThe mixture was partitioned between dichloromethane and water
  2. extractionThe aqueous layer was extracted with dichloromethane twice
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-dabd5c5c67a4466cb4ec2c5239f3c496
Source dataset
uspto-grants-1996_11
Patent number
US05574042

Reaction notes

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