Toluene → 4-(5-Chloro-2-methoxyphenyl)pyridazine

HRID 1619625

反応式

HRID 1619625 の反応式
C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].Br.Br[C:16]1[CH:21]=[CH:20][N:19]=[N:18][CH:17]=1.[Cl:22][C:23]1[CH:24]=[CH:25][C:26]([O:32][CH3:33])=[C:27](B(O)O)[CH:28]=1>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(O)C>[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([O:32][CH3:33])=[C:25]([C:16]2[CH:21]=[CH:20][N:19]=[N:18][CH:17]=2)[CH:24]=1

参加物

7

反応物 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 27357515-Chloro-2-methoxyphenylboronic acidHCID 534079064-Bromopyridazine hydrobromide

生成物 1

HCID 580422674-(5-Chloro-2-methoxyphenyl)pyridazine収率 58%

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 702Ethanol溶媒

反応条件

温度
110 °C

実験手順

To an argon purged flask containing toluene (187 mL), ethanol (20.6 mL) and a 2M aqueous solution of sodium carbonate (132.3 mL) was added 4-bromopyridazine hydrobromide (Preparation 5, 15 g, 64 mmol), 5-chloro-2-methoxybenzeneboronic acid (13.4 g, 72 mmol) and tetrakis(triphenylphosphine) palladium (0) (3.2 g, 2.8 mmol). The flask was purged with argon again, then the reaction mixture heated to 110° C. for 4 hours. The mixture was filtered through Celite™ and the filtrate concentrated in vacuo. The residue was partitioned between ethyl acetate and water. The organic layer was washed with water and brine, then dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude residue was dissolved in ethyl acetate and extracted with a 2M aqueous solution of hydrogen chloride (×3). The aqueous layer was basified with sodium hydrogen carbonate and extracted with ethyl acetate. The organic layer was then washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford the title compound (8 g, 58%).

後処理

  1. customThe flask was purged with argon again
  2. filtrationThe mixture was filtered through Celite™
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe residue was partitioned between ethyl acetate and water
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. dissolutionThe crude residue was dissolved in ethyl acetate
  10. extractionextracted with a 2M aqueous solution of hydrogen chloride (×3)
  11. extractionextracted with ethyl acetate
  12. washThe organic layer was then washed with water and brine
  13. dry with materialdried over anhydrous sodium sulfate
  14. filtrationfiltered
  15. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-b5fd5bf0c9cb498c85a9ce89b94337ca
出典データセット
uspto-grants-2014_07
特許番号
US08772293B2

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