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

HRID 1478543노트

반응식

HRID 1478543 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d453ee0bbda44dab920dc6c73f81c1dc
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09403845B2

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