Phosphorus oxybromide → ethyl 6-bromo-2-methylpyridine-3-carboxylate

HRID 339992Notes

Reaction equation

HRID 339992 reaction equation
[CH3:1][C:2]1[NH:3][C:4](=O)[CH:5]=[CH:6][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].P(Br)(Br)([Br:16])=O.C([O-])(O)=O.[Na+]>>[Br:16][C:4]1[CH:5]=[CH:6][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:2]([CH3:1])[N:3]=1

Participants

4

Reactant 3

HCID 24613Phosphorus oxybromideHCID 516892Sodium BicarbonateHCID 3299500ethyl 2-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate

Product 1

HCID 72212511ethyl 6-bromo-2-methylpyridine-3-carboxylateYield 93.1%

Conditions

Temperature
130 °C

Procedure

Ethyl 2-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate (2.0 g, 11 mmol) and POBr3 (8.9 g, 31 mmol) were mixed in one 100 mL flask, and the mixture was stirred at 130° C. for 4 hrs. The reaction mixture was cooled to room temperature and 50 g of ice water was added. The mixture was neutralized to pH=9 with aqueous NaHCO3 solution, extracted twice with EtOAc, dried over sodium sulfate, filtered and concentrated under reduced pressure to give 2.5 g (93% yield) of the desired product. LC-MS found: 244.1 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted twice with EtOAc
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d0055a56544d46d886e7e110499b8846
Source dataset
uspto-grants-2014_11
Patent number
US08895571B2

Reaction notes

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