Water → tert-Butyl 3-[(4-bromo-2-oxopyridin-1(2H)-yl)methyl]piperidine-1-carboxylate

To a solution of 2-hydroxy-4-bromopyridine (0.10 g, 0.57 mmol) in DMSO (1.50 mL) was added KOH (0.095 g, 1.70 mmol) and the resulting reaction mixture was stirred for 10 min at room temperature followed by addition of 1-Boc-3-bromomethylpiperidine (0.16 g, 0.57 mmol). The reaction mixture was then stirred at 45° C. for 16 h. After the completion of reaction (TLC monitoring), water was added to the reaction and extracted with EtOAc (3×25 mL). The combined organics was washed with brine, dried (Na2SO4), filtered and concentrated. The residue was purified over silica gel (100-200 M, 1% MeOH-DCM) to obtain the desired product (0.15 g, 95%). MS: 371.10 (M+H)+.

1. customthe resulting reaction mixture
2. stirringThe reaction mixture was then stirred at 45° C. for 16 h
3. additionwas added to the reaction
4. extractionextracted with EtOAc (3×25 mL)
5. washThe combined organics was washed with brine
6. dry with materialdried (Na2SO4)
7. filtrationfiltered
8. concentrationconcentrated
9. customThe residue was purified over silica gel (100-200 M, 1% MeOH-DCM)

ORD-Eintrag

ord-8aae24412ae143088d3032618860ce99

Quelldatensatz

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08299065B2