Potassium Carbonate → HCID 178465732、化合物

HRID 2376684ノート

反応式

HRID 2376684 の反応式
[CH2:1]([NH:3][S:4]([C:7]1[CH:12]=[CH:11][C:10](Br)=[CH:9][CH:8]=1)(=[O:6])=[O:5])[CH3:2].C([O-])(=O)C.[K+].[CH3:19][O:20][C:21]1[CH:26]=[CH:25][N:24]=[C:23]([CH2:27][CH2:28][C:29]2[NH:38][C:32]3=[N:33][CH:34]=[C:35](I)[CH:36]=[C:31]3[N:30]=2)[CH:22]=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]>[CH2:1]([NH:3][S:4]([C:7]1[CH:12]=[CH:11][C:10]([C:35]2[CH:36]=[C:31]3[N:30]=[C:29]([CH2:28][CH2:27][C:23]4[CH:22]=[C:21]([O:20][CH3:19])[CH:26]=[CH:25][N:24]=4)[NH:38][C:32]3=[N:33][CH:34]=2)=[CH:9][CH:8]=1)(=[O:6])=[O:5])[CH3:2]

参加物

10

反応物 5

HCID 11430Potassium CarbonateHCID 74803Benzenesulfonamide, p-bromo-N-ethyl-HCID 433294Lithium ChlorideHCID 517044Potassium AcetateHCID 178493175HCID 178493175、化合物2 回

生成物 1

HCID 178465732HCID 178465732、化合物収率 58.1%

試薬・触媒・溶媒 4

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒2 回HCID 312751,4-Dioxane溶媒2 回

反応条件

温度
90 °C

実験手順

A mixture of 0.348 g of N-ethyl4-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 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(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 25-15:1). Concentration of the chromatographically pure fractions and crystallisation from ethylacetate gives 0.248 g of the title compound as a solid of m.p. 214-216° C. The mass spectrum shows the molecular peak MH+ at 438.4 Da.

後処理

  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 25-15:1)
  8. customConcentration of the chromatographically pure fractions and crystallisation from ethylacetate

出典と根拠

ORDレコード
ord-1c0c3e58ba9c47ddb5f150055325540e
出典データセット
uspto-grants-2008_12
特許番号
US07468377B2

反応ノート

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