Potassium Carbonate → HCID 21082088, compound

HRID 347014Notes

Reaction equation

HRID 347014 reaction equation
[Br-].[NH2:2][C:3]1[CH:12]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=2)[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH:20]([C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=3)[C:21]3[N:25]([CH3:26])[CH:24]=[N:23][N:22]=3)[CH:9]=2)[N+:4]=1[CH2:34][C:35](=O)[C:36]([O:38][CH2:39][CH3:40])=[O:37].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[Cl:19][C:15]1[CH:14]=[C:13]([C:11]2[C:10]3[C:5](=[CH:6][CH:7]=[C:8]([CH:20]([C:27]4[CH:28]=[CH:29][C:30]([Cl:33])=[CH:31][CH:32]=4)[C:21]4[N:25]([CH3:26])[CH:24]=[N:23][N:22]=4)[CH:9]=3)[N:4]3[CH:34]=[C:35]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[N:2]=[C:3]3[CH:12]=2)[CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 21082014HCID 21082014, compound

Product 1

HCID 21082088HCID 21082088, compoundYield 27.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of intermediate (67) (0.0006 mol), obtained in Example A12 g, in ethanol (3 ml) was stirred and refluxed for 18 hours. Potassium carbonate 10% was added. The mixture was extracted with DCM. The organic layer was separated, dried (MgSO4), filtered, and the solvent was evaporated till dryness. The residue (0.3 g) was purified by column chromatography over kromasil (eluent: CH2Cl2 100 to CH2Cl2/CH3OH 90/10; 10 μm). The pure fractions were collected and the solvent was evaporated. The residue (0.12 g, 33%) was crystallized from CH3CN/DIPE. The precipitate was filtered off and dried, yielding 0.091 g (25%) of ethyl 5-(3-chlorophenyl)-7-[(4-chlorophenyl)(4-methyl-4H-1,2,4-triazol-3-yl)methyl]-imidazo[1,2-a]quinoline-2-carboxylate, mp. 220° C.

Workup

  1. temperaturerefluxed for 18 hours
  2. extractionThe mixture was extracted with DCM
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated till dryness
  7. customThe residue (0.3 g) was purified by column chromatography over kromasil (eluent: CH2Cl2 100 to CH2Cl2/CH3OH 90/10; 10 μm)
  8. customThe pure fractions were collected
  9. customthe solvent was evaporated
  10. customThe residue (0.12 g, 33%) was crystallized from CH3CN/DIPE
  11. filtrationThe precipitate was filtered off
  12. customdried

Sources & evidence

ORD record
ord-3bdfe5cbd3874f77b8e535fff902f503
Source dataset
uspto-grants-2007_02
Patent number
US07173040B2

Reaction notes

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