Trichloroacetonitrile → (+/-)-1-(5-Bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-7-yl)ethyl 2,2,2-trichloroacetimidate
Reaction equation
[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]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
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.
Workup
- concentrationthe reaction was concentrated
- custompurified by column chromatography (10% EtOAc/Hex+0.5% Et3N)
- customto give 780 mg (98%) as a colorless film
Sources & evidence
- ORD record
- ord-4c94385a9d654be183223b4721dcfb64
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08026257B2
Reaction notes
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