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

HRID 1478543ノート

反応式

HRID 1478543 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d453ee0bbda44dab920dc6c73f81c1dc
出典データセット
uspto-grants-2016_08
特許番号
US09403845B2

反応ノート

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