Water → 3-Chloro-6-(4-chlorophenyl)pyridazine

HRID 271703

반응식

HRID 271703 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](OB(O)O)=[CH:4][CH:3]=1.[Cl:12][C:13]1[N:14]=[N:15][C:16](Cl)=[CH:17][CH:18]=1.C([O-])([O-])=O.[Na+].[Na+].O>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:12][C:13]1[N:14]=[N:15][C:16]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[CH:17][CH:18]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 673313,6-DichloropyridazineHCID 17810664p-Chlorophenylboric acid

생성물 1

HCID 122575023-Chloro-6-(4-chlorophenyl)pyridazine

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 312751,4-Dioxane용매2회

반응 조건

온도
110 °C

실험 절차

Under an argon atmosphere a solution of 11.3 g (70.5 mmol) 4-chlorophenylboric acid in 50 mL 1,4-dioxane is added to a solution of 10.8 g (70.5 mmol) 3,6-dichloropyridazine, 10 mL (20 mmol) of a 2 M Na2CO3 solution and 600 mg (0.73 mmol) Pd(dppf)Cl2 in 150 mL 1,4-dioxane at 110° C. over 2 h. The reaction mixture is stirred for 1 h at 110° C. 100 mL water are added and the aqueous phase is extracted with 100 mL EtOAc. The organic phase is dried over Na2SO4 and the solvent is eliminated i.vac. Purification is carried out by column chromatography on silica gel (cyc/EtOAc 4:1).

후처리

  1. extractionthe aqueous phase is extracted with 100 mL EtOAc
  2. dry with materialThe organic phase is dried over Na2SO4
  3. customPurification

출처 및 근거

ORD 기록
ord-58f9c3b7b7de47869439a62f3987251e
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07452911B2

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