1,2-Dimethoxyethane → Imidazo[1,2-a]pyridine,7-[4-(methylsulfonyl)phenyl]-

HRID 1446660Notes

Reaction equation

HRID 1446660 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]2[CH:8]=[CH:9][N:10]=[C:4]2[CH:3]=1.[CH3:11][S:12]([C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1)(=[O:14])=[O:13].C(=O)([O-])[O-].[Cs+].[Cs+].COCCOC>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCO>[CH3:11][S:12]([C:15]1[CH:20]=[CH:19][C:18]([C:2]2[CH:7]=[CH:6][N:5]3[CH:8]=[CH:9][N:10]=[C:4]3[CH:3]=2)=[CH:17][CH:16]=1)(=[O:14])=[O:13]

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10796Cesium carbonateHCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 196959017-Chloroimidazo(1,2-a)pyridine

Product 1

HCID 68543695Imidazo[1,2-a]pyridine,7-[4-(methylsulfonyl)phenyl]-Yield 361.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Procedure

Heat a mixture of 7-chloro-imidazo[1,2-a]pyridine (100 g, 152.5 mmol, 1 eq), 4-methylsulfonylphenyl boronic acid (157.3 g, 786.8 mmol, 1.2 eq), Pd(PPh3)4 (19 g, 16.3 mmol, 0.025 eq) and cesium carbonate (472.4 g, 1.44 mol, 2.2 eq) in a mixture of anhydrous DME (2000 mL) and EtOH (1000 mL) at 80° C. under N2 atmosphere for 24 hours. Cool the mixture to room temperature and filter through Celite® to remove Pd catalyst. Add water (5000 mL) and extract this solution with CH2Cl2 (3×2000 mL). Dry the organic phase over MgSO4 and evaporate. Add to the crude 2000 mL of CH2Cl2 and heat to reflux. Remove insoluble materials by filtration and evaporate the solvent to afford a yellow solid. Wash the solid with ethyl ether to give 150 g of the desired compound as a light yellow solid. (Yield: 85%). MS (ES), m/z 273 (M+1).

Workup

  1. temperatureHeat
  2. filtrationfilter through Celite®
  3. customto remove Pd catalyst
  4. extractionAdd water (5000 mL) and extract this solution with CH2Cl2 (3×2000 mL)
  5. dry with materialDry the organic phase over MgSO4
  6. customevaporate
  7. additionAdd to the crude 2000 mL of CH2Cl2
  8. temperatureheat to reflux
  9. filtrationRemove insoluble materials by filtration
  10. customevaporate the solvent
  11. customto afford a yellow solid
  12. washWash the solid with ethyl ether

Sources & evidence

ORD record
ord-0a444651b2b04a7e98389084d73b58dc
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

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