Potassium Carbonate → HCID 178493138, compound

HRID 722039Notes

Reaction equation

HRID 722039 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.[NH2:21][C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[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[NH:20][C:14]3=[N:15][CH:16]=[C:17]([C:25]4[CH:26]=[CH:27][C:22]([NH2:21])=[CH:23][CH:24]=4)[CH:18]=[C:13]3[N:12]=2)[CH:4]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 433294Lithium ChlorideHCID 27346154-Aminophenylboronic acidHCID 178493135HCID 178493135, compound

Product 1

HCID 178493138HCID 178493138, compoundYield 52.3%

Reagents, catalysts & solvents 3

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

Procedure

0.166 g of 2-[2-(4-methoxypyridin-2-yl)ethyl]-6-bromo-3H-imidazo[4,5-b]pyridine (example 6) and 0.13 g of 4-aminophenylboronic acid are dissolved in 8 ml of degassed dioxane. Then a solution of 0.21 g of potassium carbonate and 0.042 g of lithium chloride in 6.5 ml of degassed water and 0.058 g of tetrakis(triphenylphosphine)palladium(0) are added. The mixture is heated to reflux under N2 for 24 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 30–15:1). Concentration of the chromatographically pure fractions gives 0.09 g of the title compound as a yellow solid of m.p. 117–119° C. The mass spectrum shows the molecular peak MH+ at 346.3 Da.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux under N2 for 24 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 30–15:1)

Sources & evidence

ORD record
ord-3d79b938477e403ea37171829bd7a4b3
Source dataset
uspto-grants-2006_11
Patent number
US07138399B2

Reaction notes

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