Reacción #2491608

Ecuación de reacción

2-[(3-bromophenyl)(1-methylpiperidin-4-yloxy)methyl]benzothiazole

Xantphos

benzyl mercaptan

diisopropylethylamine

→

2-[(3-benzylsulfanylphenyl)(1-methylpiperidin-4-yloxy)methyl]benzothiazole

Disolventes

1,4-dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe tube is evacuated
2. 2
   workup.ADDITIONfilled with argon
3. 3
   Otrosealed
4. 4
   workup.ADDITIONthe mixture is diluted with ethyl acetate and water
5. 5
   Extracciónthe aqueous phase is extracted with ethyl acetate
6. 6
   SecadoThe pooled organic extracts are dried over magnesium sulfate
7. 7
   Concentraciónconcentrated under reduced pressure
8. 8
   OtroThe residue is purified by chromatography (gradient dichloromethane/methanol/ammonia from 100/0/0 to 95/5/0.5)
9. 9
   OtroThe residual yellowish oil is re-crystallized from hot acetonitrile

Procedimiento

A screw-cap tube is charged with 2-[(3-bromophenyl)(1-methylpiperidin-4-yloxy)methyl]benzothiazole (208 mg), palladium bis(dibenzylideneacetone) (14 mg), Xantphos (14 mg), benzyl mercaptan (59 μL), diisopropylethylamine (174 μL) and 1,4-dioxane (2 mL). The tube is evacuated, filled with argon and sealed. After stirring at 120° C. for 15 h, the mixture is diluted with ethyl acetate and water and the aqueous phase is extracted with ethyl acetate. The pooled organic extracts are dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by chromatography (gradient dichloromethane/methanol/ammonia from 100/0/0 to 95/5/0.5). The residual yellowish oil is re-crystallized from hot acetonitrile to give 2-[(3-benzylsulfanylphenyl)(1-methylpiperidin-4-yloxy)methyl]benzothiazole melting at 195° C.

Fuente