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Potassium Carbonate → 3-(3-Ethynylphenyl)-2-(2,4,6-trifluorobenzyl)-7-(trifluoromethyl)-2H-indazole

HRID 735449
Notes
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Reaction equation

HRID 735449 reaction equation
[F:1][C:2]1[CH:33]=[C:32]([F:34])[CH:31]=[C:30]([F:35])[C:3]=1[CH2:4][N:5]1[C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]#[C:21][Si](C)(C)C)[CH:15]=2)=[C:12]2[C:7]([C:8]([C:26]([F:29])([F:28])[F:27])=[CH:9][CH:10]=[CH:11]2)=[N:6]1.C(=O)([O-])[O-].[K+].[K+]>CO>[C:20]([C:16]1[CH:15]=[C:14]([C:13]2[N:5]([CH2:4][C:3]3[C:30]([F:35])=[CH:31][C:32]([F:34])=[CH:33][C:2]=3[F:1])[N:6]=[C:7]3[C:12]=2[CH:11]=[CH:10][CH:9]=[C:8]3[C:26]([F:29])([F:27])[F:28])[CH:19]=[CH:18][CH:17]=1)#[CH:21]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 866030102-(2,4,6-Trifluorobenzyl)-7-(trifluoromethyl)-3-{3-[(trimethylsilyl)ethynyl]phenyl}-2H-indazole

Product 1

HCID 866030133-(3-Ethynylphenyl)-2-(2,4,6-trifluorobenzyl)-7-(trifluoromethyl)-2H-indazoleYield 91.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-(2,4,6-trifluorobenzyl)-7-(trifluoromethyl)-3-{3-[(trimethylsilyl)-ethynyl]phenyl}-2H-indazole (1.78 g, 3.54 mmol) and potassium carbonate (0.49 g, 3.54 mmol) in 50 mL of methanol was heated at 50° C. for 2 hours. The reaction mixture was concentrated in vacuo and the residue partitioned between ethyl acetate and H2O. The organic phase was dried (Na2SO4) and concentrated in vacuo to give 1.4 g of a white solid, which was purified by flash chromatography (silica gel 60, hexane-ethyl acetate, 4:1) to give 1.1 g of the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue partitioned between ethyl acetate and H2O
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f6c3b4208cae47368f783b6806385578
Source dataset
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07592363B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes