Reaktion #1749393

Reaktionsgleichung

4-bromo-2-trifluoromethylpyridine

t-butyllithium

(E)-N-((3-bromo-4-methoxyphenyl)(2-cyano-3-fluorophenyl)methylene)-2-methylpropane-2-sulfinamide

Hydrochloric acid

methanol

→

title compound

Ausbeute 89.3%

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

Ausbeute 89.3%

Lösungsmittel

THF

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITThe reaction mixture was left on a thawing
2. 2
   Temperaturcooling bath for 1 hour
3. 3
   Sonstigeto reach room temperature
4. 4
   workup.STIRRINGthe reaction was stirred for 1 hour
5. 5
   workup.ADDITIONSilica powder was added
6. 6
   Einengenthe mixture was concentrated under reduced pressure
7. 7
   SonstigeThe residue was purified by flash column chromatography (0-10% 0.1M NH3 in methanol in DCM)

Vorschrift

A solution of 4-bromo-2-trifluoromethylpyridine (1.76 g, 7.80 mmol) in THF (2 mL) was added dropwise at −100° C. to t-butyllithium (9.17 mL, 15.59 mmol) in THF (15 mL) followed by the addition of (E)-N-((3-bromo-4-methoxyphenyl)(2-cyano-3-fluorophenyl)methylene)-2-methylpropane-2-sulfinamide (3.1 g, 7.09 mmol) in THF (10 mL). The reaction mixture was left on a thawing cooling bath for 1 hour and then allowed to reach room temperature and stirred for 2.5 hours. Hydrochloric acid in methanol (1.25 M, 28.4 mL, 35.4 mmol) was added and the reaction was stirred for 1 hour. Silica powder was added and the mixture was concentrated under reduced pressure. The residue was purified by flash column chromatography (0-10% 0.1M NH3 in methanol in DCM) to afford the title compound (3.04 g, 89%).

Quelle