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

HRID 1993363노트

반응식

HRID 1993363 반응식
[F:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[Cl:13][C:14]1[N:15]=[N:16][C:17](Cl)=[CH:18][CH:19]=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:13][C:14]1[N:15]=[N:16][C:17]([C:4]2[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([F:1])[CH:3]=2)=[CH:18][CH:19]=1

참가 물질

7

반응물 2

HCID 673313,6-DichloropyridazineHCID 27821943-Fluoro-4-methoxyphenylboronic acid

생성물 1

HCID 203982843-Chloro-6-(3-fluoro-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 3-fluoro-4-methoxyphenylboronic acid (10 g, 0.059 mol) and 3,6-dichloro-pyridazine (8.79 g, 0.059 mol) in 2 M Na2CO3/EtOH/toluene (80 mL/40 mL/200 mL) was bubbled through N2 for 5 min. Cat. Pd(PPh3)4 (3.47 g, 0.003 mol) was added under N2 and the reaction was heated to 80° C. for 16 h. The mixture was diluted with 200 mL of EtOAc and 40 mL of water. The organic phase was separated, washed with 80 mL of brine, dried over Na2SO4 and concentrated in vacuo. The solid obtained was washed with 50% EtOAc/hexane to provide off-white solid. MS (ESI pos. ion) m/z: 239.0 (M+H). Calc'd Exact Mass for C11H8ClFN2O: 238.65.

후처리

  1. customwas bubbled through N2 for 5 min
  2. customThe organic phase was separated
  3. washwashed with 80 mL of brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe solid obtained
  7. washwas washed with 50% EtOAc/hexane
  8. customto provide off-white solid

출처 및 근거

ORD 기록
ord-8af5266fe87e48ff985cff11eec9634e
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07652009B2

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