Potassium Carbonate → HCID 178465732, compound

HRID 2376684Notes

Reaction equation

HRID 2376684 reaction equation
[CH2:1]([NH:3][S:4]([C:7]1[CH:12]=[CH:11][C:10](Br)=[CH:9][CH:8]=1)(=[O:6])=[O:5])[CH3:2].C([O-])(=O)C.[K+].[CH3:19][O:20][C:21]1[CH:26]=[CH:25][N:24]=[C:23]([CH2:27][CH2:28][C:29]2[NH:38][C:32]3=[N:33][CH:34]=[C:35](I)[CH:36]=[C:31]3[N:30]=2)[CH:22]=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].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:1]([NH:3][S:4]([C:7]1[CH:12]=[CH:11][C:10]([C:35]2[CH:36]=[C:31]3[N:30]=[C:29]([CH2:28][CH2:27][C:23]4[CH:22]=[C:21]([O:20][CH3:19])[CH:26]=[CH:25][N:24]=4)[NH:38][C:32]3=[N:33][CH:34]=2)=[CH:9][CH:8]=1)(=[O:6])=[O:5])[CH3:2]

Participants

10

Reactant 5

HCID 11430Potassium CarbonateHCID 74803Benzenesulfonamide, p-bromo-N-ethyl-HCID 433294Lithium ChlorideHCID 517044Potassium AcetateHCID 178493175HCID 178493175, compound2×

Product 1

HCID 178465732HCID 178465732, compoundYield 58.1%

Reagents, catalysts & solvents 4

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
90 °C

Procedure

A mixture of 0.348 g of N-ethyl4-bromobenzenesulfonamide, 0.42 g of bis-pinacolato)diboron, 0.025 g of 1,1′-bis-(diphenylphosphino)-ferrocene, 0.033 g of [1,1′-bis(diphenylphosphino)-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 17 hours. To the resulting mixture 5 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 5 ml of degassed water are added under N2. The tube is sealed again, the mixture is heated to 115° under N2 for 7 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 25-15:1). Concentration of the chromatographically pure fractions and crystallisation from ethylacetate gives 0.248 g of the title compound as a solid of m.p. 214-216° C. The mass spectrum shows the molecular peak MH+ at 438.4 Da.

Workup

  1. customThe tube is sealed again
  2. temperaturethe mixture is heated to 115° under N2 for 7 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 25-15:1)
  8. customConcentration of the chromatographically pure fractions and crystallisation from ethylacetate

Sources & evidence

ORD record
ord-1c0c3e58ba9c47ddb5f150055325540e
Source dataset
uspto-grants-2008_12
Patent number
US07468377B2

Reaction notes

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