Water → HCID 22485172, compound

HRID 2181021Notes

Reaction equation

HRID 2181021 reaction equation
CN(C)[CH:3]=[O:4].[C:6]1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Br[C:36]1[N:41]=[C:40]2[N:42]([CH2:47][C:48]3[CH:53]=[CH:52][C:51]([O:54][CH2:55][CH2:56][CH3:57])=[CH:50][C:49]=3[Cl:58])[C:43]([CH2:45][CH3:46])=[N:44][C:39]2=[CH:38][CH:37]=1.[C]=O.[OH2:61]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CO.C(N(CC)CC)C>[Cl:58][C:49]1[CH:50]=[C:51]([O:54][CH2:55][CH2:56][CH3:57])[CH:52]=[CH:53][C:48]=1[CH2:47][N:42]1[C:40]2=[N:41][C:36]([C:6]([O:4][CH3:3])=[O:61])=[CH:37][CH:38]=[C:39]2[N:44]=[C:43]1[CH2:45][CH3:46]

Participants

9

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 812191,3-Bis(diphenylphosphino)propaneHCID 22485175HCID 22485175, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 22485172HCID 22485172, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 887MethanolSolventHCID 8471TriethylamineSolvent

Procedure

N,N-Dimethylformamide (6 ml), triethylamine(0.85 ml), 1,3-bis(diphenylphosphino)propane (346 mg), palladium (II) acetate (188 mg) and methanol(4 ml) were added to 5-bromo-3-(2-chloro-4-(1-propoxy)benzyl)-2-ethyl-3H-imidazo[4,5-b]pyridine (1.07 g) and the mixture was stirred for 8 hr while heating to 85° C. in a 10 atm. carbon monoxide atmosphere. After cooling with ice, water (20 ml) was added to the reaction mixture and the reaction mixture was stirred at room temperature. The precipitated crystals were collected by filtration, washed with water and air-dried. This was applied to silica gel column chromatography, eluted with hexane/ethyl acetate=1/1, and concentrated under reduced pressure. Methanol (5 ml) was added to the obtained crystals and heated on a hot water bath. The mixture was stirred under ice-cooling, and the precipitate was collected by filtration and washed with cooled methanol to give methyl 3-(2-chloro-4-(1-propoxy)benzyl)-2-ethyl-3H-imidazo[4,5-b]pyridine-5-carboxylate as bright yellow crystals (816 mg).

Workup

  1. additionwas added to the reaction mixture
  2. stirringthe reaction mixture was stirred at room temperature
  3. filtrationThe precipitated crystals were collected by filtration
  4. washwashed with water
  5. customair-dried
  6. washeluted with hexane/ethyl acetate=1/1
  7. concentrationconcentrated under reduced pressure
  8. additionMethanol (5 ml) was added to the obtained crystals
  9. temperatureheated on a hot water bath
  10. stirringThe mixture was stirred under ice-
  11. temperaturecooling
  12. filtrationthe precipitate was collected by filtration
  13. washwashed with cooled methanol

Sources & evidence

ORD record
ord-fc183e016c2f42d1a6a906cc139ad2a1
Source dataset
uspto-grants-2005_05
Patent number
US06890934B2

Reaction notes

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