Potassium bis(trimethylsilyl)amide → 6-Bromo-4-hydroxy-1,5-naphthyridin-2(1H)-one

HRID 1478543Notes

Reaction equation

HRID 1478543 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[K+].[C:11]([NH:14][C:15]1[C:16]([C:22]([O:24]CC)=O)=[N:17][C:18]([Br:21])=[CH:19][CH:20]=1)(=[O:13])[CH3:12]>C1COCC1>[Br:21][C:18]1[N:17]=[C:16]2[C:15](=[CH:20][CH:19]=1)[NH:14][C:11](=[O:13])[CH:12]=[C:22]2[OH:24]

Participants

4

Reactant 2

HCID 3251421Potassium bis(trimethylsilyl)amideHCID 90044467Ethyl 3-acetamido-6-bromopyridine-2-carboxylate

Product 1

HCID 900429756-Bromo-4-hydroxy-1,5-naphthyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of KHMDS (0.5 M in toluene, 27 ml, 14 mmol) at −78° C. was slowly added a solution of ethyl 3-acetamido-6-bromo-pyridine-2-carboxylate (1.3 g, 4.5 mmol) in THF (20 ml). Stirring was continued for 1 h at this temperature then the cooling bath was removed. Ethyl acetate followed by water was added at ambient temperature, then the phases were separated. The yellow aqueous phase was treated with HCl (1 M) until a colorless solid was formed. Filtration and washing of the solid with water followed by drying afforded 6-bromo-4-hydroxy-1H-1,5-naphthyridin-2-one as a colorless solid. The compound is exclusively present in the tautomer shown.

Workup

  1. customthe cooling bath was removed
  2. additionwas added at ambient temperature
  3. customthe phases were separated
  4. additionThe yellow aqueous phase was treated with HCl (1 M) until a colorless solid
  5. customwas formed
  6. filtrationFiltration
  7. washwashing of the solid with water
  8. customby drying

Sources & evidence

ORD record
ord-d453ee0bbda44dab920dc6c73f81c1dc
Source dataset
uspto-grants-2016_08
Patent number
US09403845B2

Reaction notes

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