3-(3-bromophenyl)-2-(2,4,6-trifluorobenzyl)-7-(trifluoromethyl)-2H-indazole → 2-(2,4,6-Trifluorobenzyl)-7-(trifluoromethyl)-3-{3-[(trimethylsilyl)ethynyl]phenyl}-2H-indazole

HRID 735448Notes

Reaction equation

HRID 735448 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[N:9]([CH2:21][C:22]3[C:27]([F:28])=[CH:26][C:25]([F:29])=[CH:24][C:23]=3[F:30])[N:10]=[C:11]3[C:16]=2[CH:15]=[CH:14][CH:13]=[C:12]3[C:17]([F:20])([F:19])[F:18])[CH:5]=[CH:6][CH:7]=1.[CH3:31][Si:32]([C:35]#[CH:36])([CH3:34])[CH3:33].C([Sn](CCCC)CCCC)CCC>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:28][C:27]1[CH:26]=[C:25]([F:29])[CH:24]=[C:23]([F:30])[C:22]=1[CH2:21][N:9]1[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([C:36]#[C:35][Si:32]([CH3:34])([CH3:33])[CH3:31])[CH:3]=2)=[C:16]2[C:11]([C:12]([C:17]([F:19])([F:18])[F:20])=[CH:13][CH:14]=[CH:15]2)=[N:10]1

Participants

5

Reactant 2

HCID 866030113-(3-bromophenyl)-2-(2,4,6-trifluorobenzyl)-7-(trifluoromethyl)-2H-indazoleHCID 86603012Trimethylsilyl-acetylene tributyltin

Product 1

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

Reagents, catalysts & solvents 2

HCID 178420534HCID 178420534, compoundCatalystHCID 1140TolueneSolvent

Procedure

A solution of 3-(3-bromophenyl)-2-(2,4,6-trifluorobenzyl)-7-(trifluoromethyl)-2H-indazole (2.0 g, 4.1 mmol) and trimethylsilyl-acetylene-tributyltin in 30 mL of toluene was degassed. Palladium-tetrakis-triphenylphosphine (0.046 g, 0.4 mmol) was added and the mixture heated at reflux for 18 hours. The reaction mixture was concentrated in vacuo and purified by flash chromatography (silica 60, hexane-ethyl acetate, 9:1) to give the title compound (1.8 g) as a white solid.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 18 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. custompurified by flash chromatography (silica 60, hexane-ethyl acetate, 9:1)

Sources & evidence

ORD record
ord-00c69510130b4a74889c182e8ef8fcac
Source dataset
uspto-grants-2009_09
Patent number
US07592363B2

Reaction notes

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