反応式
Cl[C:2]1[C:3]([O:8][CH:9]2[CH2:12][N:11]([C:13]3[CH:22]=[CH:21][C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[N:14]=3)[CH2:10]2)=[N:4][CH:5]=[CH:6][N:7]=1.C(N(CC)CC)C.[CH2:30]([OH:33])[C:31]#[CH:32]>[Cu]I>[N:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:21]=[CH:22][C:13]=1[N:11]1[CH2:12][CH:9]([O:8][C:3]2[C:2]([C:32]#[C:31][CH2:30][OH:33])=[N:7][CH:6]=[CH:5][N:4]=2)[CH2:10]1参加物
反応物 3
生成物 1
試薬・触媒・溶媒 1
反応条件
- 温度
- 110 °C
実験手順
A microwave tube was charged with 2-(3-((3-chloropyrazin-2-yl)oxy)azetidin-1-yl)quinoline (see PREPARATION P2.6; 150 mg, 0.5 mmol), triethylamine (100 mg, 1.0 mmol), CuI (10 mg, 0.05 mmol), Pd (PPh3)2Cl2 (35 mg, 0.05 mmol), prop-2-yn-1-ol (28 mg, 0.05 mmol). After several cycles of vacuum/purge with argon, 2 mL of DMF are added. The reaction mixture is then stirred at 110° C. under microwave for 2 hours. The reaction mixture is poured onto a solution of NaHCO3 and diluted with EtOAc and the layers are separated. The organic extracts were washed with water (10 mL) and brine (10 mL), dried over Na2SO4, and filtered. The filtrate was evaporated in vacuo and the residue was purified by flash column chromatography on silica gel (5% to 30% EtOAc in petroleum ether) to give the title product (99 mg, 0.3 mmol, 61% yield) as white solid. ESI-MS (M+1): 333 calc. for C19H16N4O2 332.
後処理
- customAfter several cycles of vacuum/purge with argon, 2 mL of DMF
- additionare added
- additionThe reaction mixture is poured onto a solution of NaHCO3
- additiondiluted with EtOAc
- customthe layers are separated
- washThe organic extracts were washed with water (10 mL) and brine (10 mL)
- dry with materialdried over Na2SO4
- filtrationfiltered
- customThe filtrate was evaporated in vacuo
- customthe residue was purified by flash column chromatography on silica gel (5% to 30% EtOAc in petroleum ether)
出典と根拠
- ORDレコード
- ord-bce3d9b9183341fa93009bcbf97a746a
- 出典データセット
- uspto-grants-2013_07
- 特許番号
- US08497265B2
関連ノート
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