Dimethylformamide → 6-methoxy-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-4-carbonitrile

Temperature

145 °C

A sealed microwave vial was charged with 4-bromo-6-methoxy-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole (1.50 g, 4.82 mmol), Zn(CN)2 (0.62 g, 5.30 mmol), Pd(PPh3)4 (0.22 g, 0.19 mmol), and DMF (13 mL). The mixture was degassed for 5 min under nitrogen and then heated in a microwave reactor at 145° C. for 25 min. The mixture was diluted with EtOAc and filtered. The filtrate was partitioned between water and EtOAc, and the layers were separated. The organic layer was washed with water (3×), dried (Na2SO4), filtered, and concentrated in vacuo. The crude mixture was purified by SiO2 chromatography to afford 6-methoxy-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-4-carbonitrile as a solid (1.06 g, 86%). MS (ESI) m/z: 258.2 [M+1]+.

1. customThe mixture was degassed for 5 min under nitrogen
2. additionThe mixture was diluted with EtOAc
3. filtrationfiltered
4. customThe filtrate was partitioned between water and EtOAc
5. customthe layers were separated
6. washThe organic layer was washed with water (3×)
7. dry with materialdried (Na2SO4)
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customThe crude mixture was purified by SiO2 chromatography

ORD record

ord-21c7529ae68c47449bb2c436c7520d4b

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08637537B2