Phenol → 3-(3-Fluoro-4-methoxy-phenyl)-6-phenoxy-pyridazine

HRID 1993367노트

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HRID 1993367 반응식
Cl[C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([F:16])[CH:9]=2)=[CH:6][CH:7]=1.[C:17]1([OH:23])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.CCOC(C)=O>[F:16][C:10]1[CH:9]=[C:8]([C:5]2[N:4]=[N:3][C:2]([O:23][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:7][CH:6]=2)[CH:13]=[CH:12][C:11]=1[O:14][CH3:15]

참가 물질

6

반응물 3

HCID 996PhenolHCID 10796Cesium carbonateHCID 203982843-Chloro-6-(3-fluoro-4-methoxyphenyl)pyridazine

생성물 1

HCID 574454003-(3-Fluoro-4-methoxy-phenyl)-6-phenoxy-pyridazine

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
150 °C

실험 절차

A mixture of 3-chloro-6-(3-fluoro-4-methoxy-phenyl)-pyridazine (1.0 g, 4019 mmol), phenol (0.26 g, 5.03 mmol) and Cs2CO3 (1.64 g, 5.03 mmol) in 15 mL of DMF (in microwave tube) was heated in a microwave (Personal Chemistry, Emrys Optimizer) at 150° C. for 15 min. The mixture was cooled to RT and diluted with 60 mL of EtOAc. The solution was washed with 20 mL of satd. NaHCO3 followed by 20 mL of brine, dried over Na2SO4 and concentrated in vacuo. The solid was washed with 50% EtOAc/hexanes to provide the title compound as an off-white solid. MS (ESI pos. ion) m/z: 297.3 (M+H). Calc'd Exact Mass for C17H13FN2O2: 296.30.

후처리

  1. temperatureThe mixture was cooled to RT
  2. washThe solution was washed with 20 mL of satd
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. washThe solid was washed with 50% EtOAc/hexanes

출처 및 근거

ORD 기록
ord-925058e3e1864a10aeeacdf2e0ac1a6f
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07652009B2

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