Potassium Carbonate → HCID 21882692, compound

HRID 722044Notes

Reaction equation

HRID 722044 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](I)[CH:18]=[C:13]3[N:12]=2)[CH:4]=1.[CH2:21]([O:28][C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][C:30]=1[F:38])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.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[N:20]([C:32]3[CH:33]=[CH:34][C:29]([O:28][CH2:21][C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)=[C:30]([F:38])[CH:31]=3)[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[N:12]=2)[CH:4]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 433294Lithium ChlorideHCID 27377884-Benzyloxy-3-fluorophenylboronic AcidHCID 178493175HCID 178493175, compound

Product 1

HCID 21882692HCID 21882692, compoundYield 46.2%

Reagents, catalysts & solvents 3

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

Procedure

0.38 g of 2-[2-(4-methoxypyridin-2-yl)ethyl]-6-iodo-3H-imidazo[4,5-b]pyridine (example 7) and 0.37 g of 4-benzyloxy-3-fluorophenylboronic acid are dissolved in 16 ml of degassed dioxane. Then a solution of 0.276 g of potassium carbonate and 0.85 g of lithium chloride in 13 ml of degassed water and 0.115 g of tetrakis(triphenylphosphine)palladium(0) are added. The mixture is heated to reflux under N2 for 18 hours and, after cooling, addition of water and adjusting the pH to 7, 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 28:1). Concentration of the chromatographically pure fractions and crystallisation from ethyl acetate gives 0.21 g of the title compound as a yellowish solid of m.p. 168–170° C. The mass spectrum shows the molecular peak MH+ at 455.3 Da.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux under N2 for 18 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 28:1)
  8. customConcentration of the chromatographically pure fractions and crystallisation from ethyl acetate

Sources & evidence

ORD record
ord-fce2fcc44f5f4a16bb56d2638fe40070
Source dataset
uspto-grants-2006_11
Patent number
US07138399B2

Reaction notes

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