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

HRID 1619625

반응식

HRID 1619625 반응식
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

참가 물질

7

반응물 4

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

생성물 1

HCID 580422674-(5-Chloro-2-methoxyphenyl)pyridazine수율 58%

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 702Ethanol용매

반응 조건

온도
110 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-b5fd5bf0c9cb498c85a9ce89b94337ca
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772293B2

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