Potassium Phosphate, Tribasic → HCID 131735087, Verbindung

Temperatur

100 °C

A vial was charged with [(3R,3aR,6R,6aS)-3-[1-allyl-5-(4-bromophenyl)-6-chloro-imidazo[4,5-b]pyridin-2-yl]oxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-6-yl]oxy-tert-butyl-dimethyl-silane (508.1 mg, 0.837 mmol), tert-butyl 4,6-dihydro-2H-pyrrolo[3,4-c]pyrazole-5-carboxylate (213.1 mg, 1.018 mmol), tripotassium phosphate (603.1 mg, 2.84 mmol), and copper(I) iodide (33.2 mg, 0.174 mmol). The vial was evacuated and backfilled with nitrogen (3×). Trans-N,N′-dimethylcyclohexane-1,2-diamine (53 μl, 0.335 mmol) and dioxane (1.6 ml) were added to the vial to give a pale blue suspension that was heated at 100° C. with stirring for 24 h. The reaction mixture was cooled to room temperature and partitioned between EtOAc (100 ml) and water (100 ml). The aqueous layer was extracted with EtOAc (2×50 ml). The organic layers were combined, washed with brine (1×30 ml), dried over MgSO4, filtered, and evaporated under reduced pressure to give a light green residue. Flash chromatography of the residue utilizing an 40 g silica RediSep Rf® column and employing a 0-40% EtOAc/hexane gradient followed by 40% EtOAc/hexane afforded the desired product as a white foam. LC-MS: calculated for C37H47ClN6O6Si 734.3 observed m/e: 735.34 (M+H)+ (Rt 1.47/2 min)

1. customThe vial was evacuated
2. customto give a pale blue suspension that
3. temperatureThe reaction mixture was cooled to room temperature
4. custompartitioned between EtOAc (100 ml) and water (100 ml)
5. extractionThe aqueous layer was extracted with EtOAc (2×50 ml)
6. washwashed with brine (1×30 ml)
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. customevaporated under reduced pressure
10. customto give a light green residue

ORD-Eintrag

ord-105129ceb7b047ae8a9f9a2274df99a0

Quelldatensatz

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09290517B2