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Cesium carbonate → 2,2-dimethyl-1-[2-(2-pyrrolidin-1-yl-pyridin-4-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one

HRID 547475
ノート
印刷プレビュー

反応式

HRID 547475 の反応式
N1C2[C:4](=[CH:5]C=CC=2)[C:3]([C:10]2[N:11]=[C:12]3[C:18]([C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:17][N:16](COCC[Si](C)(C)C)[C:13]3=[N:14][CH:15]=2)=C1.C(=O)([O-])[O-].[Cs+].[Cs+].[H-].[Na+].[H][H]>C(#N)C.C1(C)C=CC=CC=1.CC(C)=O>[CH3:22][C:20]([CH3:21])([CH3:23])[C:19]([C:18]1[C:12]2[C:13](=[N:14][CH:15]=[C:10]([C:3]3[CH:3]=[CH:10][N:11]=[C:5]([N:16]4[CH2:17][CH2:18][CH2:12][CH2:13]4)[CH:4]=3)[N:11]=2)[NH:16][CH:17]=1)=[O: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 4

HCID 10796Cesium carbonateHCID 24758Sodium hydrideHCID 578295791-[2-(1H-indol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-oneHCID 178418361HCID 178418361、化合物

生成物 1

HCID 441923402,2-dimethyl-1-[2-(2-pyrrolidin-1-yl-pyridin-4-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one収率 35.9%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 20247278Toluene acetone溶媒

反応条件

温度
80 °C

実験手順

Step 2—A mixture of 1-[2-(1H-indol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one (0.2 g, 0.446 mmol), 1 (0.23 g, 0.892 mmol), and cesium carbonate (0.29 g, 0.892 mmol) in 4 mL of acetonitrile was stirred at 80° C. overnight. TLC (hexanes/EtOAc 7/3) showed little conversion, so NaH 60% dispersion in oil (0.067 g, 1.672 mmol) was added and the after hydrogen evolution had stopped the reaction mixture was stirred at 130° C. under microwave irradiation for two hours before being cooled to RT. The reaction mixture was partitioned between EtOAc and saturated aqueous ammonium chloride, the aqueous layer was back extracted twice with EtOAc. Combined organic layers were dried over Na2SO4, filtered and evaporated. The residue was purified by SiO2 chromatography (hexanes/EtOAc 0-20% EtOAc) and then a second time (toluene/acetone 0-10% acetone) to give 0.028 g of 2 (10% yield)

後処理

  1. additionwas added
  2. stirringwas stirred at 130° C. under microwave irradiation for two hours
  3. temperaturebefore being cooled to RT
  4. customThe reaction mixture was partitioned between EtOAc and saturated aqueous ammonium chloride
  5. extractionthe aqueous layer was back extracted twice with EtOAc
  6. dry with materialCombined organic layers were dried over Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by SiO2 chromatography (hexanes/EtOAc 0-20% EtOAc)

出典と根拠

ORDレコード
ord-14631894312147b48cd97ad5a63875b6
出典データセット
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07939531B2

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