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 735448Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 735448
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

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178420534HCID 178420534, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-00c69510130b4a74889c182e8ef8fcac
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592363B2

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