Potassium Carbonate → HCID 178493151, compound

HRID 1179405Notes

Reaction equation

HRID 1179405 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]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[CH:18]=3)[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C([O-])(=O)C.[K+].[CH3:30][O:31][C:32]1[CH:37]=[CH:36][N:35]=[C:34]([CH2:38][CH2:39][C:40]2[NH:49][C:43]3=[N:44][CH:45]=[C:46](I)[CH:47]=[C:42]3[N:41]=2)[CH:33]=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>[Cl:24][C:19]1[CH:18]=[C:17]([N:14]2[CH2:15][CH2:16][N:11]([S:8]([C:5]3[CH:6]=[CH:7][C:2]([C:46]4[CH:47]=[C:42]5[N:41]=[C:40]([CH2:39][CH2:38][C:34]6[CH:33]=[C:32]([O:31][CH3:30])[CH:37]=[CH:36][N:35]=6)[NH:49][C:43]5=[N:44][CH:45]=4)=[CH:3][CH:4]=3)(=[O:10])=[O:9])[CH2:12][CH2:13]2)[CH:22]=[C:21]([Cl:23])[CH:20]=1

Participants

10

Reactant 5

HCID 11430Potassium CarbonateHCID 433294Lithium ChlorideHCID 517044Potassium AcetateHCID 68411193HCID 68411193, compoundHCID 178493175HCID 178493175, compound2×

Product 1

HCID 178493151HCID 178493151, compoundYield 8.4%

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 0.675 g of 1-(4-bromo-benzene-sulfonyl)-4-(3,5-dichlorphenyl)-piperazine, 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 8 ml of degassed dioxane are heated to 85° C. in a sealed tube under N2 for 6 hours. To the resulting mixture 4 ml of degassed dioxane, 0.342 g of 2-[2-(4-methoxypyridin-2-yl)ethyl]-6-iodo-3H-imidazo[4,5b]pyridine (starting material A1), 0.104 g of tetrakis(triphenylphosphine)-palladium(0) and a solution of 0.25 g of potassium carbonate and 0.076 g of lithium chloride in 4 ml of degassed water are added under N2. The tube is sealed again, the mixture is heated to 110° under N2 for 17 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 28-24:1). Concentration of the chromatographically pure fractions and crystallization of the residue from ethylacetate gives 0.047 g of the title compound as a solid of m.p. 220-222° C. The mass spectrum shows the molecular peak MH+ at 623.5 Da.

Workup

  1. customThe tube is sealed again
  2. temperaturethe mixture is heated to 110° under N2 for 17 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 28-24:1)
  8. customConcentration of the chromatographically pure fractions and crystallization of the residue from ethylacetate

Sources & evidence

ORD record
ord-bb0db9fbf19344cf9dc984b84b5e5320
Source dataset
uspto-grants-2007_10
Patent number
US07279488B2

Reaction notes

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