HCID 67358291, compound → HCID 67357839, compound

HRID 1185993Notes

Reaction equation

HRID 1185993 reaction equation
O[CH:2]([C:6]1([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)[N:10]2[CH:11]=[C:12]([C:15]([O:17][CH3:18])=[O:16])[CH:13]=[CH:14][C:9]2=[N:8][CH2:7]1)[C:3]([OH:5])=[O:4]>C(O)=O.[Pd]>[CH3:18][O:17][C:15]([C:12]1[CH:13]=[CH:14][C:9]2[N:10]([C:6]([CH2:2][C:3]([OH:5])=[O:4])([C:19]3[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][CH:24]=3)[CH2:7][N:8]=2)[CH:11]=1)=[O:16]

Participants

4

Reactant 1

HCID 67358291HCID 67358291, compound

Product 1

HCID 67357839HCID 67357839, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 284Formic AcidSolvent

Procedure

To a solution of 4 (8.5 g, 25 mmol) in formic acid (100 ml) under nitrogen was added 10% palladium/carbon catalyst (600 mg) and the mixture heated at reflux overnight. The mixture was cooled to room temperature, filtered and evaporated to dryness. Water (100 ml) was added and the mixture stirred for 2 h. The white precipitate was filtered, washed with water (2×50 ml) and dried to give the light brown/yellow solid 2-[6-methoxycarbonyl-3-(4-tolyl)imidazo[1,2-a]pyridine-3-yl]acetic acid 5 (7.9 g, 97%).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux overnight
  3. filtrationfiltered
  4. customevaporated to dryness
  5. additionWater (100 ml) was added
  6. filtrationThe white precipitate was filtered
  7. washwashed with water (2×50 ml)
  8. customdried

Sources & evidence

ORD record
ord-45ea17bfe196414d834bc17062081bc5
Source dataset
uspto-grants-2014_03
Patent number
US08673652B2

Reaction notes

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