1-(2-Bromopyridin-3-yl)propane-1,3-diol → 3,4-dihydro-2H-pyrano[2,3-b]pyridin-4-ol
Reaction equation
Br[C:2]1[C:7]([CH:8]([OH:12])[CH2:9][CH2:10][OH:11])=[CH:6][CH:5]=[CH:4][N:3]=1.C(O[K])(C)(C)C>CC(O)(C)C>[O:11]1[C:2]2=[N:3][CH:4]=[CH:5][CH:6]=[C:7]2[CH:8]([OH:12])[CH2:9][CH2:10]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A mixture of 1-(2-bromopyridin-3-yl)propane-1,3-diol (40.9 mmol) (Bioorg. Med. Chem. Lett., 20(9), 2938-2941, 2010) and tBuOK (123 mmol) in 164 mL tBuOH was stirred for 90 min at 80° C. The reaction mixture was then concentrated in vacuo, taken up in H2O and extracted with EtOAc and DCM. The combined organic layers were dried over MgSO4 and concentrated in vacuo. Purification by CC (KP-SIL™ from Biotage) using DCM/MeOH (1-5%) gives the desired product as brown oil;