Water → 5-Bromo-2-[(oxolan-3-yl)oxy]pyridine

HRID 333694Notes

Reaction equation

HRID 333694 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[N:6][CH:7]=1.C([O-])([O-])=O.[Cs+].[Cs+].[OH:15][CH:16]1[CH2:20][CH2:19][O:18][CH2:17]1.O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:15][CH:16]2[CH2:20][CH2:19][O:18][CH2:17]2)=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 99603-Furanol, tetrahydro-HCID 10796Cesium carbonateHCID 27831685-Bromo-2-fluoropyridine

Product 1

HCID 219142665-Bromo-2-[(oxolan-3-yl)oxy]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 5-bromo-2-fluoropyridine (1.5 mL, 14.2 mmol) in DMF (14 mL) was added Cs2CO3 (9.3 g, 28.5 mmol) and 3-hydroxytetrahydrofuran (1.7 mL, 21.3 mmol). The reaction mixture was heated at 90° C. for 3 days then allowed to cool to room temperature (rt). Water was added and product was filtered off, washed with water, and dried under vacuum overnight (3.5 g, 100%). MS (ESI): mass calcd. for C9H10BrNO2, 243.0; m/z found, 244.3, 246.3 [M+H]+. 1H NMR (CDCl3): 8.17 (d, J=2.1 Hz, 1H), 7.64 (dd, J=8.8, 2.6 Hz, 1H), 6.66 (dd, J=8.7, 0.5 Hz, 1H) 5.52-5.48 (m, 1H), 4.04-3.95 (m, 2H), 3.93-3.86 (m, 2H), 2.30-2.19 (m, 1H), 2.15-2.08 (m, 1H).

Workup

  1. temperatureto cool to room temperature (rt)
  2. filtrationproduct was filtered off
  3. washwashed with water
  4. customdried under vacuum overnight (3.5 g, 100%)

Sources & evidence

ORD record
ord-522d67c1e05e43c59289ca6c6f98db11
Source dataset
uspto-grants-2014_11
Patent number
US08883776B2

Reaction notes

Loading…