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

HRID 1993367ノート

反応式

HRID 1993367 の反応式
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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
150 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-925058e3e1864a10aeeacdf2e0ac1a6f
出典データセット
uspto-grants-2010_01
特許番号
US07652009B2

反応ノート

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