Dichloromethane → 3-(2-methoxyphenyl)-1-perhydro-2H-pyran-2-yl-1H-indazole-5-carbonitrile

To a solution of 3-bromo-1-perhydro-2H-pyran-2-yl-1H-indazole-5-carbonitrile (0.600 g, 1.96 mmol), in ethylene glycol dimethyl ether (20 mL) was added 2-methoxyphenyl boronic acid (0.447 g, 2.94 mmol), [1,1′-bis(diphenylphosphino)-ferrocene] complex with dichloromethane (1:1) (0.226 g, 0.196 mmol) and potassium phosphate (2.07 g, 9.8 mmol). The reaction mixture was heated to reflux temperature for 12 hours. The solvent was then evaporated to dryness and the residue was dissolved in 20 mL of ethyl acetate. The heterogeneous solution was washed 3 times with 10 mL of water and once with 10 mL of brine. The organic layer was dried over Na2SO4 and evaporated to dryness. The resulting brown solid was adsorbed on silica gel and purified by column chromatography (85:15 hexanes/ethyl acetate) to provide the title compound (0.539 g, 82.5% yield): ES-MS (m/z) 334 [M+1]+.

1. temperatureThe reaction mixture was heated
2. temperatureto reflux temperature for 12 hours
3. customThe solvent was then evaporated to dryness
4. dissolutionthe residue was dissolved in 20 mL of ethyl acetate
5. washThe heterogeneous solution was washed 3 times with 10 mL of water
6. dry with materialThe organic layer was dried over Na2SO4
7. customevaporated to dryness
8. custompurified by column chromatography (85:15 hexanes/ethyl acetate)

ORD-Eintrag

ord-7b0c5d8db50b43e4810ced0773785e43

Quelldatensatz

uspto-grants-2007_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07211594B2