Potassium Carbonate → HCID 178493150, compound

HRID 2233499Notes

Reaction equation

HRID 2233499 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]([C:23]#[N:24])=[CH:19][CH:18]=3)[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C([O-])(=O)C.[K+].[CH3:30][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>[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]([C:2]4[CH:3]=[CH:4][C:5]([S:8]([N:11]5[CH2:16][CH2:15][N:14]([C:17]6[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[CH:19][CH:18]=6)[CH2:13][CH2:12]5)(=[O:9])=[O:10])=[CH:6][CH:7]=4)[CH:47]=[C:42]3[N:41]=2)[CH:33]=1

Participants

10

Reactant 5

HCID 11430Potassium CarbonateHCID 433294Lithium ChlorideHCID 517044Potassium AcetateHCID 3680172HCID 3680172, compoundHCID 178493175HCID 178493175, compound2×

Product 1

HCID 178493150HCID 178493150, compoundYield 84.9%

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 0.406 g of 1-(4-bromo-benzene-sulfonyl)-4-(4-cyanophenyl)-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 18 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 110° under N2 for 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 crystallized from ethylacetate. Recrystallization from ethylacetate and then from acetonitril gives 0.295 g of the title compound as a brownish solid of m.p. 217-219° C. The mass spectrum shows the molecular peak MH+ at 580.5 Da.

Workup

  1. customThe tube is sealed again
  2. temperaturethe mixture is heated to 110° under N2 for 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 crystallized from ethylacetate
  8. customRecrystallization from ethylacetate

Sources & evidence

ORD record
ord-caf2a5ffd4c04b7b8c3779d60ae276fb
Source dataset
uspto-grants-2010_05
Patent number
US07709488B2

Reaction notes

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