反応式
[O:1]1CCC[CH2:2]1.Br[C:7]1[CH:21]=[CH:20][C:10]([CH2:11][O:12][C:13]2[C:18]([F:19])=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:9][CH:8]=1.C([Li])CCC.CN(C)C=O>O>[F:19][C:18]1[C:13]([O:12][CH2:11][C:10]2[CH:20]=[CH:21][C:7]([CH:2]=[O:1])=[CH:8][CH:9]=2)=[N:14][CH:15]=[CH:16][CH:17]=1参加物
反応条件
- 温度
- -78 °C
実験手順
To a tetrahydrofuran (40 mL) solution of 2-(4-bromo-benzyloxy)-3-fluoro-pyridine (2.03 g, 7.20 mmol) described in Manufacturing Example 149-1-1 was added n-Butyl lithium (5.04 mL, 1.6 M hexane solution, 7.92 mmol) under nitrogen atmosphere at −78° C., which was stirred for 45 minutes at −78° C. Then, N,N-dimethylformamide (725 μL, 9.36 mmol) was added to the reaction mixture at −78° C., which was stirred for 1 hour and 10 minutes while the temperature was raised to room temperature. Water was added to the reaction solution at room temperature, which was extracted with ethyl acetate. The organic layer was separated, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=2:1) to obtain the title compound (887 mg, 53%).
後処理
- stirringwhich was stirred for 1 hour and 10 minutes while the temperature
- temperaturewas raised to room temperature
- extractionwhich was extracted with ethyl acetate
- customThe organic layer was separated
- washwashed with saturated aqueous sodium chloride
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- customThe residue was purified by silica gel column chromatography (heptane:ethyl acetate=2:1)
出典と根拠
- ORDレコード
- ord-824a6ae5635e4b33942f6da94baf41c3
- 出典データセット
- uspto-grants-2010_04
- 特許番号
- US07691882B2
関連ノート
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