تفاعل #325248

معادلة التفاعل

1b

(2R,6S,13aR,14aR,16aS ,Z)-ethyl 6-(tert-butoxycarbonylamino)-2-(3-chloroquinoxalin-2-yloxy)-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a-carboxylate

2-(tributylstannyl)benzo[d]thiazole

dioxane

→

title compound

المردود 92.7%

(2R,6S,13aR,14aR,16aS,Z)-ethyl 6-(tert-butoxycarbonylamino)-5,16-dioxo-2-(3-phenylquinoxalin-2-yloxy)-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a-carboxylate

المردود 92.7%

المذيبات

MeCN

ظروف التفاعل

المعالجة

1. 1
   أخرىThe vessel was evacuated
2. 2
   workup.ADDITIONnitrogen introduced
3. 3
   أخرىThe mixture was reacted in a microwave reactor at 110 degrees C
4. 4
   غسيلwashed 3 times with hexane
5. 5
   أخرىThe MeCN layer was evaporated
6. 6
   أخرىpurified by column chromatography on silica gel (CHCl3-EtOAc gradient)

الإجراء التجريبي

To a microwave vessel was added the product from 1b (700 mg. 1.07 mmole), 2-(tributylstannyl)benzo[d]thiazole (905 mg., 2.13 mmole), palladium-tetrakis(triphenylphosphine) (113 mg., 0.11 mmole) and dioxane (5 ml.). The vessel was evacuated and nitrogen introduced, which was repeated twice. The mixture was reacted in a microwave reactor at 110 degrees C. for 1 hr. The reaction was diluted with MeCN and washed 3 times with hexane. The MeCN layer was evaporated and purified by column chromatography on silica gel (CHCl3-EtOAc gradient) to obtain the title compound (692 mg., 86% yield). MS (ESI): m/z=755.2 [M+H].

المصدر