Potassium Carbonate → HCID 178493143, compound

HRID 722042Notes

Reaction equation

HRID 722042 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH2:9][CH2:10][C:11]2[NH:20][C:14]3=[N:15][CH:16]=[C:17](Br)[CH:18]=[C:13]3[N:12]=2)[CH:4]=1.[CH3:21][O:22][C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][C:28]=1[O:29][CH3:30].C(=O)([O-])[O-].[K+].[K+].[Cl-].[Li+]>O1CCOCC1.O.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>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH2:9][CH2:10][C:11]2[NH:20][C:14]3=[N:15][CH:16]=[C:17]([C:26]4[CH:25]=[CH:24][C:23]([O:22][CH3:21])=[C:28]([O:29][CH3:30])[CH:27]=4)[CH:18]=[C:13]3[N:12]=2)[CH:4]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 433294Lithium ChlorideHCID 27347023,4-Dimethoxyphenylboronic acidHCID 178493135HCID 178493135, compound

Product 1

HCID 178493143HCID 178493143, compoundYield 30.7%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

0.50 g of 2-[2-(4-methoxypyridin-2-yl)ethyl]-6-bromo-3H-imidazo[4,5-b]pyridine (example 6) and 0.41 g of 3,4-dimethoxyphenylboronic acid are dissolved in 25 ml of degassed dioxane. Then a solution of 0.415 g of potassium carbonate and 0.127 g of lithium chloride in 19 ml of degassed water and 0.173 g of tetrakis(triphenylphosphine)palladium(0) are added. The mixture is heated to reflux under N2 for 48 hours and, after cooling and addition of water, it is extracted three times with dichloromethane. The combined organic phases are dried over sodium sulfate, concentrated and the residue is chromatographed on a silica gel column (dichloromethane/methanol 30–26:1). Concentration of the chromatographically pure fractions and crystallisation from ethyl acetate gives 0.18 g of the title compound as a yellowish solid of m.p. 185–186° C. The mass spectrum shows the molecular peaks MH+ and 2MNa+ at 391.3 and 803.0 Da.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux under N2 for 48 hours
  3. temperatureafter cooling
  4. extractionis extracted three times with dichloromethane
  5. dry with materialThe combined organic phases are dried over sodium sulfate
  6. concentrationconcentrated
  7. customthe residue is chromatographed on a silica gel column (dichloromethane/methanol 30–26:1)
  8. customConcentration of the chromatographically pure fractions and crystallisation from ethyl acetate

Sources & evidence

ORD record
ord-92b44f6a817d45688e8664f09973a479
Source dataset
uspto-grants-2006_11
Patent number
US07138399B2

Reaction notes

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