Sodium Hydroxide → 4-(4-Fluorophenyl)-2-Bromo-1-(3-Phenylpropyl)-5-(4-Pyridyl)-Imidazole
反応式
[C:1]1([CH2:7][CH2:8][CH2:9][N:10]2[C:14]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)=[C:13]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)[NH:12][C:11]2=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Br)(Br)([Br:31])=O.S1(CCCC1)(=O)=O.[OH-].[Na+]>>[F:27][C:24]1[CH:25]=[CH:26][C:21]([C:13]2[N:12]=[C:11]([Br:31])[N:10]([CH2:9][CH2:8][CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:14]=2[C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)=[CH:22][CH:23]=1参加物
反応条件
- 温度
- 40 °C
実験手順
1,3-Dihydro-1-(3-phenylpropyl)-4-(4-fluorophenyl)-5-(4-pyridyl)-2H-imidazol-2-one (100 g, 0.26 mol) was mixed with POBr3 (268.7 g, 0.93 mol) and sulfolane (200 g) and the reaction mixture was heated to a temperature of 120–125° C. for 1–2 h. Upon completion, the reaction mixture was cooled to 40° C. Cautiously, over about 30 min, 2N NaOH solution (53 g) was added. Additional 2N NaOH solution (53 g) was then added at faster rate. The reaction mixture was then cooled to 15–20° C. and 4N NaOH solution (802 g) was added to adjust the solution to pH 7–8. The aqueous phase was extracted with t-butylmethyl ether (3×143 g) and the organic phases combined. To the combined organic phase was added t-butylmethyl ether (107 g). The solution was washed with water (2×150 g), resulting in the precipitation of a solid, which was collected by filtration.
後処理
- temperaturethe reaction mixture was heated to a temperature of 120–125° C. for 1–2 h
- temperatureThe reaction mixture was then cooled to 15–20° C.
- extractionThe aqueous phase was extracted with t-butylmethyl ether (3×143 g)
- additionTo the combined organic phase was added t-butylmethyl ether (107 g)
- washThe solution was washed with water (2×150 g)
- customresulting in the precipitation of a solid, which
- filtrationwas collected by filtration
出典と根拠
- ORDレコード
- ord-80f87efb730c491abfcd7a5186465444
- 出典データセット
- uspto-grants-2006_11
- 特許番号
- US07132544B2
反応ノート
読み込み中…