Toluene → HCID 70654352、化合物

HRID 539492

反応式

HRID 539492 の反応式
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

参加物

7

反応物 4

HCID 1140TolueneHCID 27346522-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 217840962-Bromo-5-methoxybenzonitrileHCID 22031701Potassium phosphate, tribasic, monohydrate

生成物 1

HCID 70654352HCID 70654352、化合物収率 68%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-64e2c143a486468fb1914509aa94df46
出典データセット
uspto-grants-2014_10
特許番号
US08871361B2

関連ノート

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