Reaktion #76799

Reaktionsgleichung

tetramethylstannane

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

tri(o-tolyl)phosphine

lithium chloride

tetramethylstannane

→

title compound

Ausbeute 166.3%

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

Ausbeute 166.3%

Lösungsmittel

chloroform

chloroform

methanol

2-methoxyethyl ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated in a bath
2. 2
   Temperaturheating
3. 3
   workup.WAITwas continued overnight
4. 4
   FiltrationThe solution was filtered
5. 5
   Sonstigesubjected to purification by HPLC

Vorschrift

A solution containing 5′-bromospiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine] (203 mg, 0.687 mmol), tris(dibenzylidineacetone)dipalladium (0) (33 mg, 0.036 mmol), tri(o-tolyl)phosphine (95 mg, 0.312 mmol), lithium chloride (241 mg, 5.69 mmol), and tetramethylstannane (1.0 ml, 1.3 g, 7.2 mmol) in 2-methoxyethyl ether (5 ml) was heated in a bath maintained at 100° C. After 3 h, a further portion of tetramethylstannane (1 ml, 1.3 g, 7.2 mmol) was added, and heating was continued overnight. The solution was filtered, and subjected to purification by HPLC using a gradient of 0-20% 1:1:2 7M methanolic ammonia:methanol:chloroform and chloroform to obtain the title compound (120 mg, 0.519 mmol, 76%) as a pale solid: electrospray MS (m/z, relative intensity) 231 ([MH]+, 100).

Quelle