3,6-Dichloropyridazine → 3-Chloro-6-(4-methoxyphenyl)pyridazine

HRID 1993359노트

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HRID 1993359 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.[Cl:12][C:13]1[N:14]=[N:15][C:16](Cl)=[CH:17][CH:18]=1>C([O-])([O-])=O.[Na+].[Na+].CCO.C1(C)C=CC=CC=1.CCOC(C)=O.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:12][C:13]1[N:14]=[N:15][C:16]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:17][CH:18]=1

참가 물질

7

반응물 2

HCID 673313,6-DichloropyridazineHCID 201262(4-Methoxyphenyl)boronic acid

생성물 1

HCID 122575013-Chloro-6-(4-methoxyphenyl)pyridazine

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 8857Ethyl Acetate용매HCID 18778779HCID 18778779, 화합물용매

반응 조건

온도
80 °C

실험 절차

A mixture of 4-methoxyphenylboronic acid (3 g, 0.02 mol) and 3,6-dichloro-pyridazine (3.58 g, 0.024 mol) in 2 M Na2CO3/EtOH toluene (40 mL/20 mL/100 mL) was bubbled through N2 for 5 min. Pd(PPh3)4 (1.15 g, 0.001 mol) was added under N2 and the reaction was heated to 80° C. for 16 h. The mixture was diluted with 100 mL of EtOAc and 20 mL of water. The organic phase was separated, washed with 50 mL of brine, dried over Na2SO4 and concentrated in vacuo. The solid obtained was washed with 50% EtOAc/hexane to provide the title compound as off-white solid. MS (ESI pos. ion) m/z: 221.0 (M+H). Calc'd Exact Mass for C11H9ClN2O: 220.65.

후처리

  1. customwas bubbled through N2 for 5 min
  2. customThe organic phase was separated
  3. washwashed with 50 mL of brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe solid obtained
  7. washwas washed with 50% EtOAc/hexane

출처 및 근거

ORD 기록
ord-067a44854a4a4735a32477cf98651e46
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07652009B2

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