Reaktion #58052

Reaktionsgleichung

2,3,3a,4-tetrahydro-1H-pyrrolo[2,1-c]-[1,2,4]benzothiadiazin-7-ol 5,5-dioxide

[4-(cyanomethyl)phenyl]-boronic acid

pyridine

→

title product

{4-[(5,5-Dioxido-2,3,3a,4-tetrahydro-1H-pyrrolo[2,1-c][1,2,4]benzothiadiazin 7-yl)oxy]phenyl}acetonitrile

Lösungsmittel

methylene chloride

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONThe reaction mixture is diluted
2. 2
   Filtrationthe suspension is filtered
3. 3
   EinengenThe filtrate is concentrated
4. 4
   Waschenis eluted with a methylene chloride/methanol 99/1 system
5. 5
   workup.ADDITIONThe fractions containing the expected product
6. 6
   Sonstigeevaporated
7. 7
   FiltrationAfter filtering off the solid

Vorschrift

A suspension composed of 1.15 g (4.77 mmol) of 2,3,3a,4-tetrahydro-1H-pyrrolo[2,1-c]-[1,2,4]benzothiadiazin-7-ol 5,5-dioxide, 1.00 g (6.21 mmol) of [4-(cyanomethyl)phenyl]-boronic acid, 1.3 g (7.15 mmol) of copper(II) acetate, 1.16 ml (14.31 mmol) of pyridine and about 500 mg of 4 Å molecular sieve in 200 ml of methylene chloride is stirred overnight. The reaction mixture is diluted by adding a further 100 ml of methylene chloride and the suspension is filtered. The filtrate is concentrated and then directly placed on a silica column which is eluted with a methylene chloride/methanol 99/1 system. The fractions containing the expected product are combined and evaporated, and the residue is taken up in a small amount of ethyl ether. After filtering off the solid, the title product is obtained in the form of beige powder.

Quelle