Formic Acid → Methyl[3-(4-chlorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-acetate

Under an argon atmosphere, 200 mg (0.65 mmol) of the compound from Example 214A, 49 μl of formic acid (1.3 mmol), 226 μl of triethylamine (1.63 mmol) and 38 mg of tetrakis(triphenylphosphine)palladium(0) (32 μmol) are dissolved in 2 ml degassed dioxan and stirred overnight at reflux temperature. To dissolve the precipitated solid, the reaction mixture is diluted with 20 ml of methanol after cooling to RT. The palladium catalyst is filtered off and the filtrate freed of the volatile components on the rotary evaporator. The residue is stirred with 5 ml acetonitrile and then suction-filtered. The solid is washed with acetonitrile and dried under high vacuum. It corresponds to the title compound with a purity of ca. 76% (130 mg, 57% of theory) and is used in the next reaction without further purification.

1. customdegassed dioxan
2. temperatureat reflux temperature
3. dissolutionTo dissolve the precipitated solid
4. additionthe reaction mixture is diluted with 20 ml of methanol
5. filtrationThe palladium catalyst is filtered off
6. customthe filtrate freed of the volatile components on the rotary evaporator
7. stirringThe residue is stirred with 5 ml acetonitrile
8. filtrationsuction-filtered
9. washThe solid is washed with acetonitrile
10. customdried under high vacuum
11. customis used in the next reaction without further purification

ORD-Eintrag

ord-ce60cd0e97464195a4e4f5720dfa1e6c

Quelldatensatz

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08084481B2