1-(2-Bromopyridin-3-yl)propane-1,3-diol → 3,4-dihydro-2H-pyrano[2,3-b]pyridin-4-ol

HRID 1508190Notes

Reaction equation

HRID 1508190 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]1

Participants

4

Reactant 2

HCID 867218991-(2-Bromopyridin-3-yl)propane-1,3-diolHCID 178418922HCID 178418922, compound

Product 1

HCID 230491373,4-dihydro-2H-pyrano[2,3-b]pyridin-4-ol

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

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;

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. extractionextracted with EtOAc and DCM
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customPurification by CC (KP-SIL™ from Biotage)

Sources & evidence

ORD record
ord-c6eb8c6f875c482ab4af2bf318d78cb2
Source dataset
uspto-grants-2015_12
Patent number
US09221832B2

Reaction notes

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