Reaktion #76798

Reaktionsgleichung

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

tri(o-tolyl)phosphine

lithium chloride

3-(tri-n-butylstannyl)pyridine

→

title compound

Ausbeute 37.0%

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

Ausbeute 37.0%

Lösungsmittel

chloroform

chloroform

methanol

1,2-dimethoxyethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturunder reflux for 6 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] (158 mg, 0.535 mmol), tris(dibenzylidineacetone)dipalladium (0) (23 mg, 0.025 mmol), tri(o-tolyl)phosphine (66 mg, 0.217 mmol), lithium chloride (99 mg, 2.34 mmol), and 3-(tri-n-butylstannyl)pyridine (0.3 ml, approx. 0.3 g, approx. 0.82 mmol) in 1,2-dimethoxyethane (2 ml) was heated under reflux for 6 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 0-20% 1:1:2 7M methanolic ammonia:methanol:chloroform and chloroform to obtain the title compound (58 mg, 0.198 mmol, 37%) as a pale solid: electrospray MS (m/z, relative intensity) 294 ([MH]+, 80), 273 (100).

Quelle