Potassium Carbonate → HCID 178493153, compound

HRID 2233497Notes

Reaction equation

HRID 2233497 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C([O-])(=O)C.[K+].[CH3:23][O:24][C:25]1[CH:30]=[CH:29][N:28]=[C:27]([CH2:31][CH2:32][C:33]2[NH:42][C:36]3=[N:37][CH:38]=[C:39](I)[CH:40]=[C:35]3[N:34]=2)[CH:26]=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>[CH3:23][O:24][C:25]1[CH:30]=[CH:29][N:28]=[C:27]([CH2:31][CH2:32][C:33]2[NH:42][C:36]3=[N:37][CH:38]=[C:39]([C:2]4[CH:7]=[CH:6][C:5]([S:8]([N:11]5[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]5)(=[O:10])=[O:9])=[CH:4][CH:3]=4)[CH:40]=[C:35]3[N:34]=2)[CH:26]=1

Participants

10

Reactant 5

HCID 11430Potassium CarbonateHCID 433294Lithium ChlorideHCID 517044Potassium AcetateHCID 7107291-(4-Bromophenylsulfonyl)-4-methylpiperazineHCID 178493175HCID 178493175, compound2×

Product 1

HCID 178493153HCID 178493153, compoundYield 45.2%

Reagents, catalysts & solvents 4

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

Conditions

Temperature
90 °C

Procedure

A mixture of 1.12 g of 1-(4-bromo-benzene-sulfonyl)-4-methyl-piperazine, 0.978 g of bis-(pinacolato)-diboron, 0.06 g of 1,1′-bis-(diphenylphosphino)-ferrocene, 0.077 g of [1,1′-bis(diphenyl-phosphino)ferrocene]palladium-dichloride (complex with CH2Cl2), 1.03 g of potassium acetate in 40 ml of degassed dioxane are heated to 90° C. under N2 for 8 hours. To the resulting mixture 15 ml of degassed dioxane, 0.931 g of 2-[2-(4-methoxypyridin-2-yl)ethyl]-6-iodo-3H-imidazo[4,5-b]pyridine (starting material A1), 0.283 g of tetrakis(triphenylphosphine)-palladium(0) and a solution of 0.678 g of potassium carbonate and 0.208 g of lithium chloride in 15 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 15-10:1). Concentration of the chromatographically pure fractions and crystallization of the residue from ethylacetate gives 0.545 g of the title compound as a solid of m.p. 193-195° C. The mass spectrum shows the molecular peak MH+ at 493.4 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 15-10:1)
  8. customConcentration of the chromatographically pure fractions and crystallization of the residue from ethylacetate

Sources & evidence

ORD record
ord-73b8be176d62432f972e69fd9611c27c
Source dataset
uspto-grants-2010_05
Patent number
US07709488B2

Reaction notes

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