1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → HCID 58540099, Verbindung

Temperatur

90 °C

A solution of 5-(azetidin-1-ylmethyl)-1-methyl-1H-pyrazol-3-amine (292 mg, 1.76 mmol), 4-bromo-6-chloro-2-methylpyridazin-3(2H)-one (393 mg, 1.76 mmol) cesium carbonate (2.00 g, 6.15 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethlxanthene (152 mg, 0.26 mmol) in dioxane (10 ml) was flushed with argon before tris(dibenzylideneacetone)dipalladium(0) (121 mg, 0.13 mmol) was added and the resulting solution was heated at 90° C. for 18 h. The mixture was cooled to room temperature and diluted with dichloromethane (50 mL) and water. The layers were separated and the aqueous layer was extracted with dichloromethane (2×25 mL).The organic layers were combined, dried over magnesium sulfate. The resulting mixture was filtered and concentrated in vacuo. The precipitate formed was isolated by filtration, washed with ether and dried under vacuum to give 4-(5-(azetidin-1-ylmethyl)-1-methyl-1H-pyrazol-3-ylamino)-6-chloro-2-methylpyridazin-3(2H)-one (272 mg, 50%) as a light yellow solid. (M+H)+=309 m/e.

1. additionwas added
2. temperatureThe mixture was cooled to room temperature
3. customThe layers were separated
4. extractionthe aqueous layer was extracted with dichloromethane (2×25 mL).The organic layers
5. dry with materialdried over magnesium sulfate
6. filtrationThe resulting mixture was filtered
7. concentrationconcentrated in vacuo
8. customThe precipitate formed
9. customwas isolated by filtration
10. washwashed with ether
11. customdried under vacuum

ORD-Eintrag

ord-00f866e5acbc4d1d94c8e0f68a9a7eb1

Quelldatensatz

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08889682B2