Potassium Carbonate → HCID 178493167, compound

HRID 2233512Notes

Reaction equation

HRID 2233512 reaction equation
[CH3:1][N:2]([CH3:18])[S:3]([C:6]1[CH:11]=[CH:10][C:9](Br)=[CH:8][C:7]=1[O:13][C:14]([F:17])([F:16])[F:15])(=[O:5])=[O:4].C([O-])(=O)C.[K+].[CH3:24][O:25][C:26]1[CH:31]=[CH:30][N:29]=[C:28]([CH2:32][CH2:33][C:34]2[NH:43][C:37]3=[N:38][CH:39]=[C:40](I)[CH:41]=[C:36]3[N:35]=2)[CH:27]=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].[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>[CH3:24][O:25][C:26]1[CH:31]=[CH:30][N:29]=[C:28]([CH2:32][CH2:33][C:34]2[NH:43][C:37]3=[N:38][CH:39]=[C:40]([C:9]4[CH:10]=[CH:11][C:6]([S:3]([N:2]([CH3:18])[CH3:1])(=[O:5])=[O:4])=[C:7]([O:13][C:14]([F:17])([F:16])[F:15])[CH:8]=4)[CH:41]=[C:36]3[N:35]=2)[CH:27]=1

Participants

11

Reactant 5

HCID 11430Potassium CarbonateHCID 433294Lithium ChlorideHCID 517044Potassium AcetateHCID 68408168HCID 68408168, compoundHCID 178493175HCID 178493175, compound2×

Product 1

HCID 178493167HCID 178493167, compoundYield 83.5%

Reagents, catalysts & solvents 5

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
85 °C

Procedure

A mixture of 0.477 g of N,N-dimethyl-4-bromo-2-trifluormethoxybenzenesulfonamide, 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 85° C. in a sealed tube under N2 for 19 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(triphenylphosphine)-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 120° under N2 for 5.5 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 30-26:1). Concentration of the chromatographically pure fractions and crystallisation from ethylacetate gives 0.425 g of the title compound as a solid of m.p. 145-146° C. The mass spectrum shows the molecular peak MH+ at 522.3 Da.

Workup

  1. customThe tube is sealed again
  2. temperaturethe mixture is heated to 120° under N2 for 5.5 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 30-26:1)
  8. customConcentration of the chromatographically pure fractions and crystallisation from ethylacetate

Sources & evidence

ORD record
ord-9a184a1f1ab649baa1f4db4ae6b16d66
Source dataset
uspto-grants-2010_05
Patent number
US07709488B2

Reaction notes

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