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

HRID 735449Notes

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]

Participants

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

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