Pentamethyldiethylenetriamine → (4-Bromo-1-trityl-1H-imidazol-2-yl)-(5-ethyl-2-fluoro-biphenyl-3-yl)-methanol
反応式
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([F:15])=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:8]=1)[CH3:2].CN(CCN(CCN(C)C)C)C.[Li]CCCC.[Br:33][C:34]1[N:35]=[C:36]([CH:58]=[O:59])[N:37]([C:39]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH:38]=1>C1COCC1>[Br:33][C:34]1[N:35]=[C:36]([CH:58]([C:5]2[C:6]([F:15])=[C:7]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:8]=[C:3]([CH2:1][CH3:2])[CH:4]=2)[OH:59])[N:37]([C:39]([C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH:38]=1参加物
6
反応物 4
生成物 1
試薬・触媒・溶媒 1
反応条件
- 温度
- -40 °C
実験手順
To a solution of Intermediate 228.2 (85 mg, 0.424 mmol) and PMDTA (0.10 mL, 0.478 mmol) in 4 ml THF at −78° C., was added BuLi (1.4 M in hexanes, 0.334 mL, 0.467 mmol). The mixture was stirred with warming to −40° C. over 30 min, recooled to −78° C., then a solution of Intermediate 175.1 (177 mg, 0.424 mmol) in 1.5 mL THF was added. The mixture was warmed to rt over 0.5 h. The reaction was quenched with sat. NH4Cl, then was diluted with EtOAc. The organic phase was washed with H2O (2×) and brine, dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography (0 to 30% EtOAc/hexanes gradient) to afford 194 mg of Intermediate 228.3 as a colorless solid.
後処理
- customrecooled to −78° C.
- temperatureThe mixture was warmed to rt over 0.5 h
- customThe reaction was quenched with sat. NH4Cl
- additionwas diluted with EtOAc
- washThe organic phase was washed with H2O (2×) and brine
- dry with materialdried (Na2SO4)
- concentrationconcentrated
- customThe crude product was purified by flash chromatography (0 to 30% EtOAc/hexanes gradient)
出典と根拠
- ORDレコード
- ord-a0779b89c9ca47c8a9d928895df38138
- 出典データセット
- uspto-grants-2009_08
- 特許番号
- US07576098B2
反応ノート
読み込み中…