Potassium Carbonate → HCID 178464507, compound

HRID 2376681Notes

Reaction equation

HRID 2376681 reaction equation
[CH2:1]([N:3]([CH2:14][CH3:15])[S:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1Br)(=[O:6])=[O:5])[CH3:2].B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.C([O-])(=O)C.[K+].[CH3:39][O:40][C:41]1[CH:46]=[CH:45][N:44]=[C:43]([CH2:47][CH2:48][C:49]2[NH:58][C:52]3=[N:53][CH:54]=[C:55](I)[CH:56]=[C:51]3[N:50]=2)[CH:42]=1.C(=O)([O-])[O-].[K+].[K+].[Cl-].[Li+]>O1CCOCC1.O.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH2:1]([N:3]([CH2:14][CH3:15])[S:4]([C:7]1[CH:12]=[CH:11][C:10]([C:55]2[CH:56]=[C:51]3[N:50]=[C:49]([CH2:48][CH2:47][C:43]4[CH:42]=[C:41]([O:40][CH3:39])[CH:46]=[CH:45][N:44]=4)[NH:58][C:52]3=[N:53][CH:54]=2)=[CH:9][CH:8]=1)(=[O:6])=[O:5])[CH3:2]

Participants

10

Reactant 6

HCID 11430Potassium CarbonateHCID 433294Lithium ChlorideHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 263700292-bromo-N,N-diethylbenzenesulfonamideHCID 178493175HCID 178493175, compound2×

Product 1

HCID 178464507HCID 178464507, compoundYield 34.1%

Reagents, catalysts & solvents 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
90 °C

Procedure

A mixture of 0.438 g of N,N-diethylbromobenzenesulfonamide, 0.42 g of bis-(pinacolato)diboron, 0.025 g of 1,1′-bis-(diphenylphosphino)-ferrocene, 0.033 g of [1,1′-bis(diphenyl-phosphino)ferrocene]palladium-dichloride (complex with CH2Cl2), 0.442 g of potassium acetate in 6 ml of degassed dioxane are heated to 90° C. in a sealed tube under N2 for 7 hours. To the resulting mixture 10 ml of degassed dioxane, 0.371 g of 2-[2-(4-methoxypyridin-2-yl)ethyl]-6-iodo-3H-imidazo[4,5-b]pyridine (starting material A1), 0.113 g of tetrakis(triphenylphos-phine)-palladium(0) and a solution of 0.27 g of potassium carbonate and 0.083 g of lithium chloride in 10 ml of degassed water are added under N2. The mixture is heated to reflux under N2 for 16 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 30-25:1). Concentration of the chromatographically pure fractions and crystallisation from ethylacetate gives 0.155 g of the title compound as a solid of m.p. 127-129° C. The mass spectrum shows the molecular peak MH+ at 466.3 Da.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux under N2 for 16 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 30-25:1)
  8. customConcentration of the chromatographically pure fractions and crystallisation from ethylacetate

Sources & evidence

ORD record
ord-f2329cd56de04e5c918445fc29dd3818
Source dataset
uspto-grants-2008_12
Patent number
US07468377B2

Reaction notes

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