Reaktion #633159

Reaktionsgleichung

2-(2-bromomethylphenyl sulfanylmethyl) benzene

methyl-6-ethylaminonicotinate

sodium hydride

→

named compound

Ausbeute 70.0%

6-[(2-Benzylsulfanylbenzyl)ethylamino]nicotinic acid methyl ester

Ausbeute 70.0%

Lösungsmittel

DMF

DMF

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirred for 18 hours
2. 2
   SonstigeThe solution was quenched with water
3. 3
   Extraktionextracted with EtOAc (7×)
4. 4
   Waschenwashed with water and brine twice
5. 5
   Trocknendried over MgSO4
6. 6
   Sonstigeevaporated
7. 7
   Sonstigeto give a white solid
8. 8
   Sonstigethat was recrystallized from EtOAc/hexane
9. 9
   SonstigeThe solid was purified with 5% EtOAc/hexane by chromatography

Vorschrift

A solution of methyl-6-ethylaminonicotinate in (59 mg, 0.332 mmol) DMF (0.8 mL) was added to sodium hydride (12 mg, 0.293 mL) in DMF (0.8 mL) at 0° C. The reaction was stirred for 1 hour and a solution of 2-(2-bromomethylphenyl sulfanylmethyl) benzene 5 (81 mg, 0.276 mmol) in 80 μL of DMF was added. The reaction was allowed to warm to ambient temperature and stirred for 18 hours. The solution was quenched with water and extracted with EtOAc (7×). The organic layers were combined, washed with water and brine twice, dried over MgSO4 and evaporated to give a white solid that was recrystallized from EtOAc/hexane. The solid was purified with 5% EtOAc/hexane by chromatography to yield 350 mg (70%) of the named compound.

Quelle