Potassium Carbonate → HCID 178493148, compound

HRID 2233500Notes

Reaction equation

HRID 2233500 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C([O-])(=O)C.[K+].[CH3:29][O:30][C:31]1[CH:36]=[CH:35][N:34]=[C:33]([CH2:37][CH2:38][C:39]2[NH:48][C:42]3=[N:43][CH:44]=[C:45](I)[CH:46]=[C:41]3[N:40]=2)[CH:32]=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].[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:29][O:30][C:31]1[CH:36]=[CH:35][N:34]=[C:33]([CH2:37][CH2:38][C:39]2[NH:48][C:42]3=[N:43][CH:44]=[C:45]([C:2]4[CH:3]=[CH:4][C:5]([S:8]([N:11]5[CH2:12][CH2:13][N:14]([C:17]6[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=6)[CH2:15][CH2:16]5)(=[O:10])=[O:9])=[CH:6][CH:7]=4)[CH:46]=[C:41]3[N:40]=2)[CH:32]=1

Participants

10

Reactant 5

HCID 11430Potassium CarbonateHCID 433294Lithium ChlorideHCID 517044Potassium AcetateHCID 11141011-[(4-Bromophenyl)sulfonyl]-4-(4-methylphenyl)piperazineHCID 178493175HCID 178493175, compound2×

Product 1

HCID 178493148HCID 178493148, compoundYield 37.5%

Reagents, catalysts & solvents 4

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
85 °C

Procedure

A mixture of 0.395 g of 1-(4-bromo-benzene-sulfonyl)-4-(p-tolyl)-piperazine, 0.28 g of bis-(pinacolato)-diboron, 0.017 g of 1,1′-bis-(diphenylphosphino)-ferrocene, 0.022 g of [1,1′-bis(diphenyl-phosphino)ferrocene]palladium-dichloride (complex with CH2Cl2), 0.294 g of potassium acetate in 6 ml of degassed dioxane are heated to 85° C. in a sealed tube under N2 for 16 hours. To the resulting mixture 4 ml of degassed dioxane, 0.228 g of 2-[2-(4-methoxypyridin-2-yl)ethyl]-6-iodo-3H-imidazo[4,5-b]pyridine (starting material A1), 0.069 g of tetrakis(triphenylphosphine)-palladium(0) and a solution of 0.165 g of potassium carbonate and 0.051 g of lithium chloride in 4 ml of degassed water are added under N2. The tube is sealed again, the mixture is heated to 115° under N2 for 7.5 hours and, after cooling, addition of water and adjusting the pH to 7, it is extracted three times with ethylacetate. The combined organic phases are dried over sodium sulfate, concentrated and the residue is chromatographed on a silica gel column (dichloromethane/methanol 25-20:1). Concentration of the chromatographically pure fractions and crystallization of the residue from ethylacetate/diethylether gives 0.128 g of the title compound as a brownish solid of m.p. 150-154° C. The mass spectrum shows the molecular peak MH+ at 569.5 Da.

Workup

  1. customThe tube is sealed again
  2. temperaturethe mixture is heated to 115° under N2 for 7.5 hours
  3. temperatureafter cooling
  4. extractionis extracted three times with ethylacetate
  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 25-20:1)
  8. customConcentration of the chromatographically pure fractions and crystallization of the residue from ethylacetate/diethylether

Sources & evidence

ORD record
ord-0ae20b7778664d74b3dc1605c287186a
Source dataset
uspto-grants-2010_05
Patent number
US07709488B2

Reaction notes

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