Cesium carbonate → 4-(3-Benzyl-2-cyano-5-methyl-benzofuran-7-yl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 18184ノート

反応式

HRID 18184 の反応式
C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:53]([N:60]1[CH2:65][CH2:64][NH:63][CH2:62][CH2:61]1)([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54].[CH2:66]([C:73]1[C:77]2[CH:78]=[C:79]([CH3:83])[CH:80]=[C:81](Br)[C:76]=2[O:75][C:74]=1[C:84]#[N:85])[C:67]1[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1>CN(C=O)C.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]>[C:56]([O:55][C:53]([N:60]1[CH2:61][CH2:62][N:63]([C:81]2[C:76]3[O:75][C:74]([C:84]#[N:85])=[C:73]([CH2:66][C:67]4[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=4)[C:77]=3[CH:78]=[C:79]([CH3:83])[CH:80]=2)[CH2:64][CH2:65]1)=[O:54])([CH3:59])([CH3:58])[CH3:57]

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 634876Binap, (A+-)-HCID 593448943-Benzyl-7-bromo-5-methyl-benzofuran-2-carbonitrile

生成物 1

HCID 593449124-(3-Benzyl-2-cyano-5-methyl-benzofuran-7-yl)-piperazine-1-carboxylic acid tert-butyl ester収率 45%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
80 °C

実験手順

In an oven dried flask was added BINAP (racemic, 0.17 g, 0.913 mmol), cesium carbonate (0.35 g, 1.07 mmol), tris(dibenzylideneacetone)dipalladium (0.0207 g, 0.0226 mmol), 1-BOC-piperazine (0.17 g, 0.913 mmol) and 5 ml DMF. The flask was evacuated and refilled with nitrogen. 3-benzyl-7-bromo-5-methyl-benzofuran-2-carbonitrile (0.29 g, 0.90 mmol) in 5 ml DMF was added via syringe and the mixture heated to 80° C. overnight, then to 100° C. for another 24 hours. The mixture was concentrated on a rotary evaporator and purified by column chromatography (1:9 ethyl acetate/hexane) to give 4-(3-benzyl-2-cyano-5-methyl-benzofuran-7-yl)-piperazine-1-carboxylic acid tert-butyl ester (0.174 g, 45% yield) as a yellow solid.

後処理

  1. customIn an oven dried flask
  2. customThe flask was evacuated
  3. additionrefilled with nitrogen
  4. concentrationThe mixture was concentrated on a rotary evaporator
  5. custompurified by column chromatography (1:9 ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-5d5e6fac3ee94d0f999f7f0d1c6c0653
出典データセット
uspto-grants-2010_06
特許番号
US07741326B2

反応ノート

読み込み中…