Реакция #1749403

Уравнение реакции

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

Выход 39.2%

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

Выход 39.2%

Растворители

THF

THF

THF

Условия реакции

Обработка

1. 1
   ДругоеThe resulting reaction mixture
2. 2
   workup.WAITwas left on the thawing
3. 3
   Температураcooling bath for 30 min
4. 4
   Другоеthe cooling bath was removed
5. 5
   workup.STIRRINGthe mixture was stirred at rt for 1 h
6. 6
   КонцентрированиеThe mixture was concentrated
7. 7
   Другоеpurified on a silica gel column
8. 8
   Промывкаeluted with 0-10% 0.1M NH3 in MeOH in DCM

Методика

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.

Источник