Ethyl 3-({3-[2-(2,4,6-trifluorobenzyl)-7-(trifluoromethyl)-2H-indazol-3-YL]phenyl}ethynyl)benzoate → Ethyl 3-(2-{3-[2-(2,4,6-trifluorobenzyl)-7-(trifluoromethyl)-2H-indazol-3-YL]phenyl}ethyl)benzoate

HRID 735451Notes

Reaction equation

HRID 735451 reaction equation
[F:1][C:2]1[CH:40]=[C:39]([F:41])[CH:38]=[C:37]([F:42])[C:3]=1[CH2:4][N:5]1[C:13]([C:14]2[CH:15]=[C:16]([C:20]#[C:21][C:22]3[CH:23]=[C:24]([CH:30]=[CH:31][CH:32]=3)[C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:17]=[CH:18][CH:19]=2)=[C:12]2[C:7]([C:8]([C:33]([F:36])([F:35])[F:34])=[CH:9][CH:10]=[CH:11]2)=[N:6]1>CO>[F:1][C:2]1[CH:40]=[C:39]([F:41])[CH:38]=[C:37]([F:42])[C:3]=1[CH2:4][N:5]1[C:13]([C:14]2[CH:15]=[C:16]([CH2:20][CH2:21][C:22]3[CH:23]=[C:24]([CH:30]=[CH:31][CH:32]=3)[C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:17]=[CH:18][CH:19]=2)=[C:12]2[C:7]([C:8]([C:33]([F:34])([F:35])[F:36])=[CH:9][CH:10]=[CH:11]2)=[N:6]1

Participants

3

Reactant 1

HCID 86603014Ethyl 3-({3-[2-(2,4,6-trifluorobenzyl)-7-(trifluoromethyl)-2H-indazol-3-YL]phenyl}ethynyl)benzoate

Product 1

HCID 86603015Ethyl 3-(2-{3-[2-(2,4,6-trifluorobenzyl)-7-(trifluoromethyl)-2H-indazol-3-YL]phenyl}ethyl)benzoateYield 100.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of ethyl 3-({3-[2-(2,4,6-trifluorobenzyl)-7-(trifluoromethyl)-2H-indazol-3-yl]phenyl}ethynyl)benzoate (0.035 g, 0.06 mmol) and palladium dimethylamine complex (3.5 mg) (ref. Sajiki et. al. JOC, 1998, 63, 7990) in 1 mL of methanol was hydrogenated at atmospheric pressure for 24 hours. The catalyst was filtered and washed with methanol. The combined filterates were evaporated to give 35 mg of product as an oil, which solidified on standing.

Workup

  1. filtrationThe catalyst was filtered
  2. washwashed with methanol
  3. customThe combined filterates were evaporated

Sources & evidence

ORD record
ord-ed0adc6aa28846dc9907c072a06cdf16
Source dataset
uspto-grants-2009_09
Patent number
US07592363B2

Reaction notes

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