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

HRID 1465832ノート

反応式

HRID 1465832 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([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

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 531671-MethylpiperazineHCID 11348662HCID 11348662、化合物HCID 162179852-Dicyclohexylphosphino-2',6'-diisopropoxybiphenyl

生成物 1

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

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ccba6e2f6fbc48ddbacfb2035fa5d78f
出典データセット
uspto-grants-2015_04
特許番号
US08999993B2

反応ノート

読み込み中…