Potassium Carbonate → HCID 178493162, 화합물

HRID 1179421노트

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HRID 1179421 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:19])[S:9]([C:12]2[CH:17]=[CH:16][C:15](Br)=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:4][CH:3]=1.C([O-])(=O)C.[K+].[CH3:25][O:26][C:27]1[CH:32]=[CH:31][N:30]=[C:29]([CH2:33][CH2:34][C:35]2[NH:44][C:38]3=[N:39][CH:40]=[C:41](I)[CH:42]=[C:37]3[N:36]=2)[CH:28]=1.C(=O)([O-])[O-].[K+].[K+].[Cl-].[Li+]>O1CCOCC1.O.[CH-]1C=CC=C1.[CH-]1C=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>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:19])[S:9]([C:12]2[CH:17]=[CH:16][C:15]([C:41]3[CH:42]=[C:37]4[N:36]=[C:35]([CH2:34][CH2:33][C:29]5[CH:28]=[C:27]([O:26][CH3:25])[CH:32]=[CH:31][N:30]=5)[NH:44][C:38]4=[N:39][CH:40]=3)=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:4][CH:3]=1

참가 물질

11

반응물 5

HCID 11430Potassium CarbonateHCID 433294Lithium ChlorideHCID 517044Potassium AcetateHCID 684087534-Bromo-N-(4-chlorophenyl)-N-methylbenzene-1-sulfonamideHCID 178493175HCID 178493175, 화합물2회

생성물 1

HCID 178493162HCID 178493162, 화합물수율 32.6%

시약·촉매·용매 5

HCID 7611Bis(eta-cyclopentadienyl) iron촉매HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 178418228Bis(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 0.541 g of N-(4-chlorophenyl)-N-methyl-4-bromo-benzenesulfonamide, 0.42 g of bis-(pinacolato)-diboron, 0.025 g of 1,1′-bisdiphenylphosphino)-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-(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 115° under N2 for 6 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 30-25:1). Concentration of the chromatographically pure fractions and crystallisation from ethylacetate gives 0.17 g of the title compound as a solid of m.p. 191-192° C. The mass spectrum shows the molecular peak MH+ at 534.3 Da.

후처리

  1. customThe tube is sealed again
  2. temperaturethe mixture is heated to 115° under N2 for 6 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 30-25:1)
  8. customConcentration of the chromatographically pure fractions and crystallisation from ethylacetate

출처 및 근거

ORD 기록
ord-3113385fb3914854bc71a817280a3f4e
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07279488B2

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