甲苯 → HCID 70654352，化合物

HRID 539492

反应方程式

HRID 539492 反应方程式
Br[C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[C:4]#[N:5].CC1(C)C(C)(C)OB([C:20]2[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=2[NH2:22])O1.O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(C)C=CC=CC=1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[CH3:11][O:10][C:7]1[CH:8]=[CH:9][C:2]2[C:3](=[C:4]([NH2:5])[N:22]=[C:21]3[C:20]=2[CH:26]=[CH:25][CH:24]=[CH:23]3)[CH:6]=1

参与物

7

反应物 4

HCID 1140甲苯HCID 27346522-氨基苯硼酸频哪醇酯HCID 217840962-溴-5-甲氧基苯甲腈HCID 22031701磷酸三钾一水合物

产物 1

HCID 70654352HCID 70654352，化合物收率 68%

试剂、催化剂与溶剂 2

HCID 178418476HCID 178418476，化合物催化剂HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂

实验过程

2-Bromo-5-methoxybenzonitrile (1.32 g, 6.23 mmol), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (1.36 g, 6.23 mmol), bis(triphenylphosphine)palladiumdichloride (0.437 g, 0.623 mmol) and potassium phosphate monohydrate (4.30 g, 18.68 mmol) were added to toluene (30 mL) and water (3 mL). The reaction mixture was degassed with bubbled nitrogen gas for 30 minutes before being refluxed under nitrogen for 15 h. After cooling, the reaction mixture was filtered through Celite® and the organic layer was extracted with ethyl acetate. After removal of the solvents, the crude material was triturated with 40 mL of DCM followed by 50 mL of hexanes to give 8-methoxyphenanthridin-6-amine (0.95 g, 68%) as a light yellow solid. The product was confirmed by GC/MS and NMR.

后处理

  1. customThe reaction mixture was degassed with bubbled nitrogen gas for 30 minutes
  2. temperaturebefore being refluxed under nitrogen for 15 h
  3. temperatureAfter cooling
  4. filtrationthe reaction mixture was filtered through Celite®
  5. extractionthe organic layer was extracted with ethyl acetate
  6. customAfter removal of the solvents
  7. customthe crude material was triturated with 40 mL of DCM

来源与证据

ORD记录
ord-64e2c143a486468fb1914509aa94df46
来源数据集
uspto-grants-2014_10
专利号
US08871361B2

关联笔记

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