Toluene → HCID 68780336, compound

HRID 2363708Notes

Reaction equation

HRID 2363708 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]2[N:10]([CH:12]=[C:13]([C:15]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:16])[N:14]=2)[CH:11]=1)=[CH2:5])[CH3:2].C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=[O:38])=CC=1>C(O)CO>[CH3:5][C:4]1([C:6]2[CH:7]=[CH:8][C:9]3[N:10]([CH:12]=[C:13]([C:15]([NH:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[O:16])[N:14]=3)[CH:11]=2)[O:38][CH2:2][CH2:1][O:3]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 44136067HCID 44136067, compound

Product 1

HCID 68780336HCID 68780336, compoundYield 20.2%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

A mixture of 80 mg of 6-(1-ethoxyvinyl)-N-phenylimidazo[1,2-a]pyridine-2-carboxamide, 2.5 mL of toluene, 280 μL of ethylene glycol and 170 mg of para-toluenesulfonic acid is placed over molecular sieves. The mixture is refluxed for 2 hours and then cooled, filtered and diluted with 20 mL of dichloromethane and 20 mL of water, and neutralized with 2N sodium hydroxide solution. The aqueous phase is washed with dichloromethane and the combined organic phases are dried and concentrated to dryness. The residue is chromatographed on a silica cartridge, eluting with a gradient of dichloromethane and ethyl acetate of from 0/30 to 70/30 to give 17 mg of 6-(2-methyl-1,3-dioxolan-2-yl)-N-phenylimidazo[1,2-a]pyridine-2-carboxamide in the form of a white solid.

Workup

  1. temperatureThe mixture is refluxed for 2 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. additiondiluted with 20 mL of dichloromethane and 20 mL of water
  5. washThe aqueous phase is washed with dichloromethane
  6. customthe combined organic phases are dried
  7. concentrationconcentrated to dryness
  8. customThe residue is chromatographed on a silica cartridge
  9. washeluting with a gradient of dichloromethane and ethyl acetate of from 0/30 to 70/30

Sources & evidence

ORD record
ord-476b1260a7a544c0ad1822594057e330
Source dataset
uspto-grants-2014_04
Patent number
US08691990B2

Reaction notes

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