Cesium carbonate → HCID 67214262, compound

HRID 2170035Notes

Reaction equation

HRID 2170035 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](Cl)=[N:6][CH:7]=1.[OH:9][C@@H:10]1[CH2:14][CH2:13][O:12][CH2:11]1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][C@@H:10]2[CH2:14][CH2:13][O:12][CH2:11]2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 641512(-)-3-HydroxytetrahydrofuranHCID 27344145-Bromo-2-chloropyridine

Product 1

HCID 67214262HCID 67214262, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 5-bromo-2-chloropyridine (10 g, 52.1 mmol) in 100 mL of DMF was added commercially available (R)-(−)-3-hydroxytetrahydrofuran (6.87 g, 78.1 mmol) and Cs2CO3 (33.85 g, 0.104 mol), the resulting mixture was heated 90° C. for 36 hours. The solvent was concentrated and the residue was extracted with EtOAc (500 ml), washed with water (200 ml). The organic layer was dried over Na2SO4, concentrated and purified by chromatography on silica gel (eluting with Petrol ether: EtOAc=100:1) to afford 5-Bromo-2-[(R)-(tetrahydro-furan-3-yl)oxy]-pyridine (5.9 g, yield: 47%) as a solid. 1HNMR (CDCl3 400 MHz): δ8.15 (d, J=2.4 Hz, 1H), 7.61-7.64 (m, 1H), 6.64 (d, J=8.8 Hz, 1H), 5.47-5.50 (m, 1H), 3.85-4.02 (m, 4H), 2.07-2.28 (m, 2H), [α]D20=+18.5 (C=0.189, CHCl3).

Workup

  1. concentrationThe solvent was concentrated
  2. extractionthe residue was extracted with EtOAc (500 ml)
  3. washwashed with water (200 ml)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated
  6. custompurified by chromatography on silica gel (eluting with Petrol ether: EtOAc=100:1)

Sources & evidence

ORD record
ord-deb1c494435847f3a19a377fc14af37e
Source dataset
uspto-grants-2015_06
Patent number
US09050327B2

Reaction notes

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