Reaktion #1749403

Reaktionsgleichung

Hydrogen chloride

methanol

N-((5-chloro-2-cyano-3-fluorophenyl)(3-methoxyphenyl)methylene)-2-methylpropane-2-sulfinamide

4-bromo-2-trifluoromethylpyridine

tert-Butyllithium

→

title compound

Ausbeute 39.2%

6-Chloro-4-fluoro-1-(3-methoxyphenyl)-1-(2-(trifluoromethyl)pyridin-4-yl)-1H-isoindol-3-amine

Ausbeute 39.2%

Lösungsmittel

THF

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe resulting reaction mixture
2. 2
   workup.WAITwas left on the thawing
3. 3
   Temperaturcooling bath for 30 min
4. 4
   Sonstigethe cooling bath was removed
5. 5
   workup.STIRRINGthe mixture was stirred at rt for 1 h
6. 6
   EinengenThe mixture was concentrated
7. 7
   Sonstigepurified on a silica gel column
8. 8
   Wascheneluted with 0-10% 0.1M NH3 in MeOH in DCM

Vorschrift

tert-Butyllithium (1.7 M in pentane, 6.59 mL, 11.20 mmol) was added dropwise to THF (10 mL) at −100° C. under an argon atmosphere. A solution of 4-bromo-2-trifluoromethylpyridine (1.266 g, 5.60 mmol) in THF (1 mL) was added dropwise followed by the addition of N-((5-chloro-2-cyano-3-fluorophenyl)(3-methoxyphenyl)methylene)-2-methylpropane-2-sulfinamide (2 g, 5.09 mmol) in THF (6 mL). The resulting reaction mixture was left on the thawing cooling bath for 30 min then the cooling bath was removed and the mixture was stirred at rt for 1.5 h. Hydrogen chloride in methanol solution (20.36 mL, 25.45 mmol) was added and the mixture was stirred at rt for 1 h. The mixture was concentrated and purified on a silica gel column eluted with 0-10% 0.1M NH3 in MeOH in DCM to afford 870 mg (39%) of the title compound.

Quelle