4-Bromopyrazole → 4-Bromo-1-(oxan-4-yl)-1H-pyrazole

Temperature

-10 °C

4-bromo-1H-pyrazole (1 eq, 3.92 mmol, 0.5 g) is dissolved in dry DMF (5 ml) under an inert atmosphere of nitrogen. The reaction mixture is cooled down to −10° C. and sodium hydride (1 eq, 3.92 mmol, 0.157 g) is added portionwise. After 15 mins at 0° C., the reaction was warmed to R.T and stirred for 30 mins at R.T. A solution of methane sulfonic acid tetrahydro-pyran-4-yl ester (Intermediate B18, step1) (1 eq, 3.92 mmol, 0.5 g) in DMF (5 ml) is added and the reaction mixture is stirred at 95° C. overnight. The reaction mixture is quenched at 0° C. with water and extracted with DCM. This organic portion is washed with water and brine, dried over MgSO4, filtered and concentrated in vacuo. The resulting solid is triturated with MeOH and the solid filtered to afford the title compound; [M+H]+ 231/233.

1. temperaturethe reaction was warmed to R.T
2. stirringthe reaction mixture is stirred at 95° C. overnight
3. customThe reaction mixture is quenched at 0° C. with water
4. extractionextracted with DCM
5. washThis organic portion is washed with water and brine
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe resulting solid is triturated with MeOH
10. filtrationthe solid filtered

ORD record

ord-0202e1d7c1d741069e37030a679913b7

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08343966B2