Reaktion #1862202

Reaktionsgleichung

3-iodo-5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine

2-(butyldipentylstannyl)pyridine

LiCl

→

204

Ausbeute 11.0%

3-(pyridin-2-yl)-5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine

Ausbeute 11.0%

Lösungsmittel

1,4-dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe tube was flushed with nitrogen for 2 minutes
2. 2
   workup.DISTILLATIONThe solvent was distilled off
3. 3
   Sonstigethe crude product was purified via reverse phase combiflash
4. 4
   Wascheneluting with 10% to 80% CH3CN in aqueous 0.5% NH4OH solution

Vorschrift

To a microwave tube was added 3-iodo-5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine from Example 4 (120 mg, 0.37 mmol), 2-(butyldipentylstannyl)pyridine (168 mg, 0.45 mmol), Pd(PPh)3 (12 mg, 0.015 mmol), LiCl (48 mg, 1.14 mmol), CuI (12 mg, 0.06 mmol) and 1,4-dioxane (0.3 mL). The tube was flushed with nitrogen for 2 minutes and heated in a Biotage microwave at 140° C. for 15 minutes. The solvent was distilled off and the crude product was purified via reverse phase combiflash eluting with 10% to 80% CH3CN in aqueous 0.5% NH4OH solution to afford 204 as a pale red solid (11 mg, 11%). 1H NMR (400 MHz, DMSO) 1H NMR (500 MHz, DMSO) δ 14.0 (s, 1H), 9.30 (s, 1H), 9.25 (s, 1H), 8.97 (s, 1H), 8.81 (d, J=4.0 Hz, 1H), 8.62-8.61 (m, 1H), 8.45 (d, J=8.5 Hz, 1H), 8.22 (d, J=7.5 Hz, 1H), 7.97-7.94 (m, 1H), 7.55-7.53 (m, 1H), 7.45-7.43 (m, 1H). ESI MS m/z=274 (M+1)

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