Reaktion #76797

Reaktionsgleichung

5′-bromospiro[1-azabicyclo[2.2.2] octane-3,2′(3′H)-furo[2,3-b]pyridine]

tri(o-tolyl)phosphine

lithium chloride

2-(tri-n-butylstannyl)furan

→

title compound

Ausbeute 89.2%

5′-(2-Furyl)spiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine]

Ausbeute 89.2%

Lösungsmittel

chloroform

chloroform

methanol

1,2-dimethoxyethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturunder reflux for 2 h
3. 3
   SonstigeThe solution was evaporated
4. 4
   Filtrationfiltered
5. 5
   SonstigeThe filtrate was evaporated
6. 6
   Sonstigethen purified by HPLC

Vorschrift

A solution containing 5′-bromospiro[1-azabicyclo[2.2.2] octane-3,2′(3′H)-furo[2,3-b]pyridine] (103.5 mg, 0.351 mmol), tris(dibenzylidineacetone)dipalladium (0) (14 mg, 0.015 mmol), tri(o-tolyl)phosphine (44.4 mg, 0.146 mmol), lithium chloride (62 mg, 1.46 mmol), and 2-(tri-n-butylstannyl)furan (0.17 g, 0.476 mmol) in 1,2-dimethoxyethane (1 ml) was heated under reflux for 2 h. The solution was evaporated, and the residue was taken up in chloroform and filtered. The filtrate was evaporated then purified by HPLC using a gradient of 0-25% 1:1:2 7M methanolic ammonia:methanol:chloroform and chloroform to obtain the title compound (89 mg, 0.313 mmol, 89%) as a pale solid: electrospray MS (m/z, relative intensity) 283 ([MH]+, 100).

Quelle