3,5-Dibromopyridine → HCID 117667680, compound

HRID 712697Notes

Reaction equation

HRID 712697 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.[O:9]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10]1>C1COCC1>[Br:8][C:6]1[CH:7]=[C:2]([C:11]2([OH:14])[CH2:12][CH2:13][O:9][CH2:10]2)[CH:3]=[N:4][CH:5]=1

Participants

4

Reactant 2

HCID 693693,5-DibromopyridineHCID 5293923-Oxotetrahydrofuran

Product 1

HCID 117667680HCID 117667680, compoundYield 10.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cooled (−15° C.) solution of 3,5-dibromopyridine (1.2 g, 5.0 mmol) in THF (12 mL) is added a solution of isopropylmagnesium chloride-lithium chloride complex in THF (1.7 M; 2.9 mL, 4.9 mmol). The resultant mixture is stirred at −15° C. for 30 min and dihydro-furan-3-one (517 mg, 6.0 mmol) is added. After stirring for 16 h, the reaction is quenched with saturated aqueous NH4Cl solution and is extracted with EtOAc. The combined organic extracts are washed with water and brine, dried and concentrated under reduced pressure. Purification by flash column chromatography provides 125 mg of 3-(5-bromo-pyridin-3-yl)-tetrahydro-furan-3-ol.

Workup

  1. customthe reaction is quenched with saturated aqueous NH4Cl solution
  2. extractionis extracted with EtOAc
  3. washThe combined organic extracts are washed with water and brine
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-71c6f17d91f4486f8e9872dfcbee0b53
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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