Sodium Carbonate → Ethyl 3-(4-bromophenyl)-4-cyano-5-ethyl-1-methyl-1h-pyrrole-2-carboxylate

HRID 1865109ノート

反応式

HRID 1865109 の反応式
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:16])[C:8]([CH2:14][CH3:15])=[C:9]([C:12]#[N:13])[C:10]=1I)=[O:5])[CH3:2].[Br:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.C([O-])([O-])=O.[Na+].[Na+].O1CCOCC1>C(Cl)Cl.O>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:16])[C:8]([CH2:14][CH3:15])=[C:9]([C:12]#[N:13])[C:10]=1[C:21]1[CH:22]=[CH:23][C:18]([Br:17])=[CH:19][CH:20]=1)=[O:5])[CH3:2]

参加物

7

反応物 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 79599(4-Bromophenyl)boronic acidHCID 57975348HCID 57975348、化合物

生成物 1

HCID 16037629Ethyl 3-(4-bromophenyl)-4-cyano-5-ethyl-1-methyl-1h-pyrrole-2-carboxylate収率 78.9%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
80 °C

実験手順

A mixture of 4-cyano-5-ethyl-3-iodo-1-methyl-1H-pyrrole-2-carboxylic acid ethyl ester (2.0 g, 6.0 mmol, prepared in preparation 38), 4-bromophenyl boronic acid (1.32 g, 6.6 mmol), 10 mL of Na2CO3 (2M) and 20 mL of dioxane is degassed under reduced pressure (−29 inches) for 30 minutes till no bubbles. Recharge with nitrogen. Add PdCl2 (PPh)4 (0.24 mmol). Well seal the flask and heat the mixture at 80° C. overnight. After cooling, water and methylene chloride are added to the reaction mixture. It is then extracted with methylene chloride. The organic layers are combined, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue is purified by flash chromatography to provide the title compound (1.71 g, 78%). MS(ES, m/e) 361.1(M+1), 380.1(M+18). Rf=0.35 (50% ether in hexanes).

後処理

  1. customis degassed under reduced pressure (−29 inches) for 30 minutes till no bubbles
  2. customWell seal the flask
  3. temperatureAfter cooling
  4. extractionIt is then extracted with methylene chloride
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is purified by flash chromatography

出典と根拠

ORDレコード
ord-53b1d3f9659a4ab69526e05f2b302fa5
出典データセット
uspto-grants-2009_12
特許番号
US07625932B2

反応ノート

読み込み中…