Trichloroacetonitrile → (+/-)-1-(5-Bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-7-yl)ethyl 2,2,2-trichloroacetimidate
反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH:11]([OH:13])[CH3:12])[CH:10]=1)[N:7]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[N:6]=[CH:5]2.[Cl:22][C:23]([Cl:27])([Cl:26])[C:24]#[N:25].C1(C2CCCCCCCCCC=2)CCCCCCCCNN=1>ClCCl>[Cl:22][C:23]([Cl:27])([Cl:26])[C:24](=[NH:25])[O:13][CH:11]([C:9]1[CH:10]=[C:2]([Br:1])[CH:3]=[C:4]2[C:8]=1[N:7]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:20])([CH3:19])[CH3:21])[N:6]=[CH:5]2)[CH3:12]参加物
反応物 3
生成物 1
試薬・触媒・溶媒 1
実験手順
To a solution of (±)-1-(5-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-7-yl)ethanol (575 mg, 1.55 mmol) and trichloroacetonitrile (1.55 mL, 15.5 mmol) in dichloromethane (15 mL) at room temperature was added diazabicycloundecene (50 μL, 0.33 mmol). After stirring 30 min, the reaction was concentrated and purified by column chromatography (10% EtOAc/Hex+0.5% Et3N) to give 780 mg (98%) as a colorless film. 1H-NMR (CDCl3, 500 MHz) δ 8.30 (s, 1H), 7.92 (d, J=2.4, 1H), 7.79 (d, J=1.5, 1H), 7.69 (d, J=1.8, 1H), 6.67 (q, J=6.4, 1H), 6.25 (d, J=11.6, 1H), 5.70 (d, J=11.6, 1H), 3.42-3.60 (m, 3H), 1.76 (d, J=6.4, 3H), 1.19 (m, 2H), 0.75-1.02 (m, 2H), -0.06 (s, 9H); 13C NMR (126 MHz, CDCl3) δ ppm 161.2, 135.6, 133.1, 128.0, 127.9, 127.6, 123.2, 114.8, 91.4, 80.2, 72.7, 66.1, 22.5, 17.8, −1.4.
後処理
- concentrationthe reaction was concentrated
- custompurified by column chromatography (10% EtOAc/Hex+0.5% Et3N)
- customto give 780 mg (98%) as a colorless film
出典と根拠
- ORDレコード
- ord-4c94385a9d654be183223b4721dcfb64
- 出典データセット
- uspto-grants-2011_09
- 特許番号
- US08026257B2
反応ノート
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