Cesium carbonate → 6-(4-Methyl-piperazin-1-yl)-1-(toluene-4-sulfonyl)-1H-indole

HRID 1465832노트

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HRID 1465832 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([O-])([O-])=O.[Cs+].[Cs+].CC(OC1C=CC=C(OC(C)C)C=1C1C(P(C2CCCCC2)C2CCCCC2)=CC=CC=1)C.[CH3:60][N:61]1[CH2:66][CH2:65][NH:64][CH2:63][CH2:62]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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[CH3:60][N:61]1[CH2:66][CH2:65][N:64]([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)[CH2:63][CH2:62]1

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 531671-MethylpiperazineHCID 11348662HCID 11348662, 화합물HCID 162179852-Dicyclohexylphosphino-2',6'-diisopropoxybiphenyl

생성물 1

HCID 674572186-(4-Methyl-piperazin-1-yl)-1-(toluene-4-sulfonyl)-1H-indole수율 73.8%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

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온도
100 °C

실험 절차

A 250 mL round bottom flask was loaded with 6-Bromo-1-(toluene-4-sulfonyl)-1H-indole (4 g, 11.4 mmol), Cs2CO3 (7.4 g, 22.8 mmol), Pd2dba3 (0.104 g, 0.114 mmol), RuPHOS (0.106 g, 0.23 mmol), Toluene (150 mL), N-Methyl piperazine (1.9 mL, 17.2 mol), evacuated and flushed with nitrogen. Next the reaction flask was heated at 100° C., over the weekend. Analysis at this point showed that most of the starting material had converted to the product. After cooling to room temperature, the solution was diluted with EtOAc (150 mL), filtered through a pad of celite, washed with additional EtOAc (150 mL) and was evaporated. The resulting oil was chromatographed on silica gel to give the product as a thick brown oil (which crystallized on standing), 3.1 g, (73.8% yield).

후처리

  1. customevacuated
  2. customflushed with nitrogen
  3. temperatureAfter cooling to room temperature
  4. additionthe solution was diluted with EtOAc (150 mL)
  5. filtrationfiltered through a pad of celite
  6. washwashed with additional EtOAc (150 mL)
  7. customwas evaporated
  8. customThe resulting oil was chromatographed on silica gel

출처 및 근거

ORD 기록
ord-ccba6e2f6fbc48ddbacfb2035fa5d78f
출처 데이터셋
uspto-grants-2015_04
특허 번호
US08999993B2

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