Sodium Bicarbonate → 4-chloro-7-methylfuro-[3,4-b]-pyridin-5-(7H)-one

HRID 2372217Notes

Reaction equation

HRID 2372217 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6](C(Br)C)[N:5]=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+]>CS(C)=O.O>[Cl:1][C:2]1[CH:3]=[CH:4][N:5]=[C:6]2[CH:11]([CH3:12])[O:10][C:8](=[O:9])[C:7]=12

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 19902854Ethyl 4-chloro-2-(1-bromoethyl)nicotinate

Product 1

HCID 199028524-chloro-7-methylfuro-[3,4-b]-pyridin-5-(7H)-one

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A mixture of ethyl 4-chloro-2-(1-bromoethyl)nicotinate (7.45 g) and sodium bicarbonate (4.00 g) in 50 ml of DMSO is heated at 120°, under nitrogen, for 2 hours, after which it is cooled, diluted with water, filtered and extracted with ether. The combined organic layers are washed with water and concentrated. The residue is taken into ethyl acetate, washed with brine, dried, concentrated and purified by flash chromatography to give 4-chloro-7-methylfuro-[3,4-b]-pyridin-5-(7H)-one, which is then reacted with N-bromosuccinimide and 2,2'-azobis(2-methylpropionitrile), as above, to give 7-bromo-4-chloro-7-methylfuro-[3,4-b]-pyridin-5-(7H)-one.

Workup

  1. temperatureis heated at 120°, under nitrogen, for 2 hours
  2. temperatureafter which it is cooled
  3. filtrationfiltered
  4. extractionextracted with ether
  5. washThe combined organic layers are washed with water
  6. concentrationconcentrated
  7. washwashed with brine
  8. customdried
  9. concentrationconcentrated
  10. custompurified by flash chromatography

Sources & evidence

ORD record
ord-1c71f8c433a24b38bed0a32610856062
Source dataset
uspto-grants-1992_03
Patent number
US05098466

Reaction notes

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