Dimethylformamide → HCID 15512895, Verbindung

Temperatur

100 °C

To dimethylformamide (18 mL) was added 1,1-dioxo-4-(trifluoro-methanesulfonyloxy)-2-(2-trifluoromethyl-phenyl)-1,2-dihydro-1λ6-benzo[e][1,2]thiazine-3-carboxylic acid methyl ester, (1.60 g, 3.0 mmol), palladium tetrakis(triphenyl phosphine) (0.2 g, 0.17 mmol), potassium carbonate (0.7 g, 6.0 mmol), 2-methoxy-phenyl-boronic acid (0.88 g, 6.0 mmol), and toluene (50 mL). The mixture was heated to 100° C. for 30 minutes and was filtered through a pad of Celite. The filtrate and EtOAc washing solution was washed three times with saturated sodium bicarbonate solution, brine, and dried over charcoal and anhydrous magnesium sulfate. The suspension was filtered and stripped to an oil which was resuspended in ethyl acetate and ethyl ether. Insoluble material from this mixture was filtered off, and the filtrate was concentrated in vacuo to an oil. The residue was chromatographed on silica gel eluted with a mixture of ethyl acetate and hexane (25:75). The appropriate fractions were concentrated in vacuo and crystallized from ethyl ether giving a solid 1.29 g, 83% yield.

1. filtrationwas filtered through a pad of Celite
2. washThe filtrate and EtOAc washing solution was washed three times with saturated sodium bicarbonate solution, brine
3. dry with materialdried over charcoal and anhydrous magnesium sulfate
4. filtrationThe suspension was filtered
5. filtrationInsoluble material from this mixture was filtered off
6. concentrationthe filtrate was concentrated in vacuo to an oil
7. customThe residue was chromatographed on silica gel
8. washeluted with a mixture of ethyl acetate and hexane (25:75)
9. concentrationThe appropriate fractions were concentrated in vacuo

ORD-Eintrag

ord-87d420c84a7c45d492d5ae23d2d1078b

Quelldatensatz

uspto-grants-2001_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06252070B1