反応式
[C:1]([O:5][C:6]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13](B3OC(C)(C)C(C)(C)O3)[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F-].[K+].Cl[C:29]1[CH:34]=[CH:33][N:32]=[C:31]([CH3:35])[CH:30]=1>O1CCOCC1>[C:1]([O:5][C:6]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:29]3[CH:34]=[CH:33][N:32]=[C:31]([CH3:35])[CH:30]=3)[CH:14]=2)[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]参加物
反応物 3
生成物 1
試薬・触媒・溶媒 1
反応条件
- 温度
- 100 °C
実験手順
A mixture containing 1.4 mmol 5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester, 4.8 mmol potassium fluoride, 1.4 mmol 4-chloro-2-picoline (commercial) and 0.03 mmol bis(tri-tert.-butylphosphine)palladium in 5 ml deglazed dioxane was stirred at 100° C. for 1.5 hours. The solvent was removed in vacuo. The residue was taken in ethyl acetate. The mixture was washed twice with water. The aqueous layer was extracted once with ethyl acetate. The combined organic layers were dried over Na2SO4, filtered and the solvent was removed in vacuo. The crude oil was purified on a 20 g Flashpack cartridge (Eluent: Heptane/AcOEt) to afford the title compound as a yellow oil (69% yield). MS (m/e): 311.2 ([M+H]+, 100%)
後処理
- customThe solvent was removed in vacuo
- washThe mixture was washed twice with water
- extractionThe aqueous layer was extracted once with ethyl acetate
- dry with materialThe combined organic layers were dried over Na2SO4
- filtrationfiltered
- customthe solvent was removed in vacuo
- customThe crude oil was purified on a 20 g Flashpack cartridge (Eluent: Heptane/AcOEt)
出典と根拠
- ORDレコード
- ord-fd225e9de212402c8f10881cdeae5040
- 出典データセット
- uspto-grants-2009_07
- 特許番号
- US07557114B2
関連ノート
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