Dioxathion → HCID 68005898、化合物

HRID 74477ノート

反応式

HRID 74477 の反応式
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[S:11]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[CH:4][CH:3]=1.C(OP(SC1OCCOC1SP(O[CH2:43][CH3:44])(OCC)=S)(OCC)=S)C.C(=O)(O)[O-].[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].[Zn].O1CCCC1>[CH3:9][N:8]1[CH2:44][CH2:43][CH:5]([C:2]2[CH:10]=[C:9]3[C:5]([CH:6]=[CH:7][N:8]3[S:11]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)(=[O:13])=[O:12])=[CH:4][CH:3]=2)[CH2:6][CH2:7]1

参加物

7

反応物 3

HCID 6531DioxathionHCID 516892Sodium BicarbonateHCID 11348662HCID 11348662、化合物

生成物 1

HCID 68005898HCID 68005898、化合物

試薬・触媒・溶媒 3

HCID 23994Zinc触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
70 °C

実験手順

6-Bromo-1-(toluene-4-sulfonyl)-1H-indole (340 mg, 0.97 mmol), Tris(dibenzylideneacetone)dipalladium (0) (23 mg, 0.025 mmol), and (3-diethoxyphosphinothioylsulfanyl-1,4-dioxan-2-yl)sulfanyl-diethoxy-sulfanylidene-phosphorane (Ruphos) (47 mg, 0.1 mmol) were placed into a reaction container. After deaeration, the air was replaced with nitrogen. Anhydrous tetrahydrofuran (THF) (5.0 ml) and a prepared zinc reagent suspension were added thereto, and this was stirred at 70° C. for 17 hours. After cooling it to room temperature, the reaction mixture was alkalinized with an aqueous solution saturated with sodium bicarbonate. The precipitated solid was removed by filtration. The filtrate was extracted with ethyl acetate. The extract was washed with water and an aqueous solution saturated with sodium chloride, and dried over anhydrous sodium sulfate. The desiccant was removed by filtration and concentration was performed. The residue obtained by concentration under reduced pressure was purified by silica gel column chromatography. Thus, 6-(1-methyl-piperidin-4-yl)-1-(toluene-4-sulfonyl)-1H-indole was obtained as a wax-like solid (293.7 mg, 82%).

後処理

  1. temperatureAfter cooling it to room temperature
  2. customThe precipitated solid was removed by filtration
  3. extractionThe filtrate was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialan aqueous solution saturated with sodium chloride, and dried over anhydrous sodium sulfate
  6. customThe desiccant was removed by filtration and concentration
  7. customThe residue obtained by concentration under reduced pressure
  8. customwas purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-a516e50cadd74692bb9260d03316c985
出典データセット
uspto-grants-2014_09
特許番号
US08829199B2

反応ノート

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