Potassium Carbonate → HCID 178493166, 화합물

HRID 2376685노트

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HRID 2376685 반응식
[CH3:1][N:2]([CH3:14])[S:3]([C:6]1[CH:11]=[CH:10][C:9](Br)=[CH:8][C:7]=1[F:13])(=[O:5])=[O:4].C([O-])(=O)C.[K+].[CH3:20][O:21][C:22]1[CH:27]=[CH:26][N:25]=[C:24]([CH2:28][CH2:29][C:30]2[NH:39][C:33]3=[N:34][CH:35]=[C:36](I)[CH:37]=[C:32]3[N:31]=2)[CH:23]=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]>[F:13][C:7]1[CH:8]=[C:9]([C:36]2[CH:37]=[C:32]3[N:31]=[C:30]([CH2:29][CH2:28][C:24]4[CH:23]=[C:22]([O:21][CH3:20])[CH:27]=[CH:26][N:25]=4)[NH:39][C:33]3=[N:34][CH:35]=2)[CH:10]=[CH:11][C:6]=1[S:3]([N:2]([CH3:14])[CH3:1])(=[O:5])=[O:4]

참가 물질

10

반응물 5

HCID 11430Potassium CarbonateHCID 433294Lithium ChlorideHCID 517044Potassium AcetateHCID 592067474-bromo-2-fluoro-N,N-dimethylbenzenesulfonamideHCID 178493175HCID 178493175, 화합물2회

생성물 1

HCID 178493166HCID 178493166, 화합물

시약·촉매·용매 4

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매2회HCID 312751,4-Dioxane용매2회

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온도
90 °C

실험 절차

A mixture of 0.423 9 of N,N-dimethyl4-bromo-2-fluorobenzenesulfonamide, 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 90° C. in a sealed tube under N2 for 17 hours. To the resulting mixture 5 ml of degassed dioxane, 0.371 g of 2-[2-(4methoxypyridin-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 25-22:1). Concentration of the chromatographically pure fractions and crystallisation from ethylacetate gives 0.27 g of the title compound as a solid of m.p. 211-212° C. The mass spectrum shows the molecular peak MH+ at 456.3 Da.

후처리

  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 25-22:1)
  8. customConcentration of the chromatographically pure fractions and crystallisation from ethylacetate

출처 및 근거

ORD 기록
ord-4256ba55db2441de861d216f651ac7c2
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07468377B2

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