Réaction #5987

Équation de réaction

water

4-Chloropyridine hydrochloride

5-amino-1-methylindole

sodium carbonate

4-chloropyridine hydrochloride

→

solid

Rendement 53.3%

1-Methyl-5-(4-pyridinylamino)-1H-indole

Rendement 53.3%

Solvants

1-methyl-2-pyrrolidinone

Conditions de réaction

Traitement

1. 1
   Autrepreheated to 100° C
2. 2
   Autreno further reaction
3. 3
   TempératureAfter two hours the reaction mixture was cooled
4. 4
   Extractionextracted with ethyl acetate
5. 5
   SéchageThe dried (anhydrous magnesium sulfate) organic layer
6. 6
   Filtrationwas filtered
7. 7
   Autreevaporated to 12.7 g of an oil
8. 8
   LavageThe oil was eluted through silica with 10% methanol in dichloromethane via flash column chromatography
9. 9
   Autreto give the product which
10. 10
    Autrewas triturated with ether

Mode opératoire

4-Chloropyridine hydrochloride (8 g) was added to a solution of 5-amino-1-methylindole (7 g) in 75 ml 1-methyl-2-pyrrolidinone preheated to 100° C. The addition of 4-chloropyridine hydrochloride (4 g) after one hour caused no further reaction as determined by TLC. After two hours the reaction mixture was cooled, stirred with water, basified with sodium carbonate and extracted with ethyl acetate. The dried (anhydrous magnesium sulfate) organic layer was filtered and evaporated to 12.7 g of an oil. The oil was eluted through silica with 10% methanol in dichloromethane via flash column chromatography to give the product which was triturated with ether to yield 5.7 g of a solid, m.p. 202°-203° C. Recrystallization from acetonitrile yielded 5 g of product as crystals, mp 209°-211° C.

Source