Реакция #1861050

Уравнение реакции

KF

2-iodo-4-(1-methylpiperidin-4-yloxy)-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene

2-(tributylstannyl)pyridine

→

4-(1-methylpiperidin-4-yloxy)-2-pyridin-2-yl-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene

Растворители

water

toluene

Условия реакции

Обработка

1. 1
   Экстракцияthe aqueous phase is extracted three times with CH2Cl2
2. 2
   ПромывкаThe organic phase is washed with a solution of 10% KF in water, brine
3. 3
   Сушкаdried over magnesium sulphate
4. 4
   Фильтрацияfiltered
5. 5
   Другоеthe solvent is removed under reduced pressure
6. 6
   ДругоеThe residue is pre-purified by silica gel chromatography
7. 7
   Промывкаeluting with (CH2Cl2:MeOH:NH4OH) (9:1:1)

Методика

To a solution of 2-iodo-4-(1-methylpiperidin-4-yloxy)-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene (example 2A) (50 mg, 0.12 mmoles) in toluene (500 μL) in a screw-capped vial under argon are added 2-(tributylstannyl)pyridine (77 μL, 0.24 mmole), tetrakis(triphenylphosphine)palladium(0) (14 mg, 12 μmole). The reaction mixture is heated at 100° C. overnight. A solution of 10% KF in water is added, and the aqueous phase is extracted three times with CH2Cl2. The organic phase is washed with a solution of 10% KF in water, brine, dried over magnesium sulphate, filtered and the solvent is removed under reduced pressure. The residue is pre-purified by silica gel chromatography using (CH2Cl2:MeOH:NH4OH) as eluent with a gradient from (99:1:0.1) to (95:5:0.5) and the residue is submitted to a preparative thin-layer chromatography eluting with (CH2Cl2:MeOH:NH4OH) (9:1:1) to afford 4-(1-methylpiperidin-4-yloxy)-2-pyridin-2-yl-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene.

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