Dioxathion → HCID 68005898, 화합물

HRID 74477노트

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HRID 74477 반응식
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

참가 물질

7

반응물 3

HCID 6531DioxathionHCID 516892Sodium BicarbonateHCID 11348662HCID 11348662, 화합물

생성물 1

HCID 68005898HCID 68005898, 화합물

시약·촉매·용매 3

HCID 23994Zinc촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 8028Tetrahydrofuran용매

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온도
70 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-a516e50cadd74692bb9260d03316c985
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829199B2

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