ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Ethyl bromoacetate → ethyl 2-(2-cyano-3,5-dimethyl-4-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetate

HRID 1189554
ノート
印刷プレビュー

反応式

HRID 1189554 の反応式
[CH3:1][C:2]1[C:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[S:14]([N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)(=[O:16])=[O:15])=[C:5]([CH3:22])[NH:4][C:3]=1[C:23]#[N:24].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34]>CCCC[N+](CCCC)(CCCC)CCCC.[I-].CN(C=O)C.C(OCC)(=O)C>[C:23]([C:3]1[N:4]([CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[C:5]([CH3:22])=[C:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[S:14]([N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)(=[O:16])=[O:15])[C:2]=1[CH3:1])#[N:24]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 672403263,5-dimethyl-4-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrole-2-carbonitrile

生成物 1

HCID 53245904ethyl 2-(2-cyano-3,5-dimethyl-4-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetate収率 110%

試薬・触媒・溶媒 3

HCID 67553Tetrabutylammonium Iodide
触媒
HCID 6228Dimethylformamide溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

To a mixture of 3,5-dimethyl-4-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrole-2-carbonitrile (29.1 mg, 0.085 mmol), cesium carbonate (110 mg, 0.339 mmol), and TBAI (3.13 mg, 8.47 μmol) in DMF (424 μl), was added ethyl bromoacetate (14.15 μl, 0.127 mmol). The mixture was heated at 60° C. for 5 hours and then allowed to cool down to room temperature and diluted with ethyl acetate (100 ml). The resulting mixture was washed with water (50 ml×3), dried, filtered, and evaporated to give an oil. This crude oil was purified by column chromatography (0 to 50% ethyl acetate in hexanes) to give ethyl 2-(2-cyano-3,5-dimethyl-4-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetate (40.0 mg, 0.093 mmol, 110% yield).

後処理

  1. temperatureto cool down to room temperature
  2. washThe resulting mixture was washed with water (50 ml×3)
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. customto give an oil
  7. customThis crude oil was purified by column chromatography (0 to 50% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-9c247d32685a4bf6abd66a6325ea1818
出典データセット
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08674115B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート