HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 913831
Notes
Print preview

Reaction equation

HRID 913831 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([CH:11]([OH:13])[CH3:12])[C:8]2[C:4](=[CH:5][N:6]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[N:7]=2)[CH:3]=1.N12CCCN=C1CCCCC2.[Cl:33][C:34]([Cl:38])([Cl:37])[C:35]#[N:36]>C(OCC)C>[Cl:33][C:34]([Cl:38])([Cl:37])[C:35](=[NH:36])[O:13][CH:11]([C:9]1[C:8]2[C:4](=[CH:5][N:6]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:20])([CH3:19])[CH3:21])[N:7]=2)[CH:3]=[C:2]([Cl:1])[CH:10]=1)[CH3:12]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11011TrichloroacetonitrileHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 57545985(+/-)-1-(5-Chloro-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-7-yl)ethanol

Product 1

HCID 57546188(+/-)-1-(5-Chloro-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-7-yl)ethyl 2,2,2-trichloroacetimidate

Reagents, catalysts & solvents 1

HCID 3283
Diethyl Ether
Solvent

Conditions

Temperature
0 °C

Procedure

(±)-1-(5-Chloro-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-7-yl)ethanol (0.54 g, 1.65 mmol) was dissolved in diethyl ether (5 mL), cooled to 0° C. and treated with 1,8-diazabicyclo(5.4.0)undec-7-ene (50 μL, 0.33 mmol). The reaction was stirred for 10 min and treated with trichloroacetonitrile (250 μL, 2.48 mmol) dropwise over 10 min. The reaction was allowed to warm to room temperature overnight and concentrated. Flash chromatography on silica gel (5% ethyl acetate/hexanes) gave 600 mg (77%) as an oil. 1H-NMR (CDCl3, 300 MHz) δ 8.34 (s, 1H), 8.02 (s, 1H), 7.56 (d, J =1.5 Hz, 1H), 7.33 (m, 1H), 6.62 (q, J=6.2 Hz, 1H), 5.68 (s, 2H), 3.59-3.65 (m, 2H), 1.79 (m, 3H), 0.88-0.94 (m, 2H), 0.05 (s, 9H).

Workup

  1. temperatureto warm to room temperature overnight
  2. concentrationconcentrated
  3. customFlash chromatography on silica gel (5% ethyl acetate/hexanes) gave 600 mg (77%) as an oil

Sources & evidence

ORD record
ord-f115e9bcdbfc4c25a53b768386b122d5
Source dataset
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08026257B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes