تفاعل #5987

معادلة التفاعل

water

4-Chloropyridine hydrochloride

5-amino-1-methylindole

sodium carbonate

4-chloropyridine hydrochloride

→

solid

المردود 53.3%

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

المردود 53.3%

المذيبات

1-methyl-2-pyrrolidinone

ظروف التفاعل

المعالجة

1. 1
   أخرىpreheated to 100° C
2. 2
   أخرىno further reaction
3. 3
   درجة الحرارةAfter two hours the reaction mixture was cooled
4. 4
   استخلاصextracted with ethyl acetate
5. 5
   تجفيفThe dried (anhydrous magnesium sulfate) organic layer
6. 6
   ترشيحwas filtered
7. 7
   أخرىevaporated to 12.7 g of an oil
8. 8
   غسيلThe oil was eluted through silica with 10% methanol in dichloromethane via flash column chromatography
9. 9
   أخرىto give the product which
10. 10
    أخرىwas triturated with ether

الإجراء التجريبي

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.

المصدر