Methyl vinyl ketone → (E)-4-(4-Amino-6-bromopyridin-3-yl)but-3-en-2-one

HRID 523078ノート

反応式

HRID 523078 の反応式
[NH2:1][C:2]1[C:7](I)=[CH:6][N:5]=[C:4]([Br:9])[CH:3]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(C(C)C)CC)(C)C.[CH:41]([C:43]([CH3:45])=[O:44])=[CH2:42]>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[NH2:1][C:2]1[CH:3]=[C:4]([Br:9])[N:5]=[CH:6][C:7]=1/[CH:42]=[CH:41]/[C:43](=[O:44])[CH3:45]

参加物

7

反応物 4

HCID 6570Methyl vinyl ketoneHCID 80271Tri-o-tolylphosphineHCID 81531DiisopropylethylamineHCID 601457042-Bromo-5-iodopyridin-4-amine

生成物 1

HCID 89995621(E)-4-(4-Amino-6-bromopyridin-3-yl)but-3-en-2-one収率 78.8%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

4-Amino-2-bromo-5-iodopyridine (4.49 g 15 mmol), tri-o-tolylphosphine (363 mg 1.2 mmol) and palladium acetate (135 mg 0.60 mmol) were dissolved in DMF (45 mL) and di-isopropylethylamine (3.76 mL, 21.6 mmol) and methyl vinyl ketone (2.45 mL, 30 mmol) were added. The reaction was placed under nitrogen and heated at 80° C. for 70 minutes. The reaction was cooled and concentrated in vacuo. Ethyl acetate (150 mL) was added and the solution was washed with water (80 mL). The organic layer was collected, washed with water (2×60 mL) brine, dried over sodium sulfate and concentrated in vacuo. The residue was triturated with ether (2×10 mL) to afford the title compound (2.85 g, 78%).

後処理

  1. temperatureThe reaction was cooled
  2. concentrationconcentrated in vacuo
  3. additionEthyl acetate (150 mL) was added
  4. washthe solution was washed with water (80 mL)
  5. customThe organic layer was collected
  6. washwashed with water (2×60 mL) brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue was triturated with ether (2×10 mL)

出典と根拠

ORDレコード
ord-39c8a259e15245b1893146337a1fccc5
出典データセット
uspto-grants-2016_05
特許番号
US09334286B2

反応ノート

読み込み中…