Trichloroacetonitrile → (+/-)-1-(5-Bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-7-yl)ethyl 2,2,2-trichloroacetimidate

HRID 913843노트

반응식

HRID 913843 반응식
[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]

참가 물질

5

반응물 3

HCID 11011TrichloroacetonitrileHCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-eneHCID 57546085(+/-)-1-(5-Bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-7-yl)ethanol

생성물 1

HCID 57546156(+/-)-1-(5-Bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-7-yl)ethyl 2,2,2-trichloroacetimidate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  1. concentrationthe reaction was concentrated
  2. custompurified by column chromatography (10% EtOAc/Hex+0.5% Et3N)
  3. customto give 780 mg (98%) as a colorless film

출처 및 근거

ORD 기록
ord-4c94385a9d654be183223b4721dcfb64
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08026257B2

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