Potassium Carbonate → HCID 178493144, compound

HRID 2376683Notes

Reaction equation

HRID 2376683 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C([O-])(=O)C.[K+].[CH3:17][O:18][C:19]1[CH:24]=[CH:23][N:22]=[C:21]([CH2:25][CH2:26][C:27]2[NH:36][C:30]3=[N:31][CH:32]=[C:33](I)[CH:34]=[C:29]3[N:28]=2)[CH:20]=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]>[CH3:17][O:18][C:19]1[CH:24]=[CH:23][N:22]=[C:21]([CH2:25][CH2:26][C:27]2[NH:36][C:30]3=[N:31][CH:32]=[C:33]([C:2]4[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][CH:3]=4)[CH:34]=[C:29]3[N:28]=2)[CH:20]=1

Participants

10

Reactant 5

HCID 11430Potassium CarbonateHCID 696964-BromobenzenesulfonamideHCID 433294Lithium ChlorideHCID 517044Potassium AcetateHCID 178493175HCID 178493175, compound2×

Product 1

HCID 178493144HCID 178493144, compoundYield 20%

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
125 °C

Procedure

A mixture of 0.354 g of 4-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 125° C. in a sealed tube under N2 for 16 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 12:1+1% NH4OH). Concentration of the chromatographically pure fractions gives 0.08 g of the title compound as a brownish solid of m.p. 216-218° C. The mass spectrum shows the molecular peak MH+ at 410.2 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 12:1+1% NH4OH)

Sources & evidence

ORD record
ord-79307c6cc4b94f40b2b05c1eb826b4af
Source dataset
uspto-grants-2008_12
Patent number
US07468377B2

Reaction notes

Loading…