3-Bromo-4-fluorobenzaldehyde → 2-benzyl-5-(3-bromo-4-fluorophenyl)-2,3,5,7,8,9-hexahydro-1H-cyclopenta[b][1,7]naphthyridine-4,6-dione

HRID 635971노트

반응식

HRID 635971 반응식
[NH2:1][C:2]1[CH2:6][CH2:5][C:4](=[O:7])[CH:3]=1.[Br:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[F:17])[CH:12]=O.[CH2:18]([N:25]1[CH2:30][C:29](=O)[CH2:28][C:27](=[O:32])[CH2:26]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(O)C>[CH2:18]([N:25]1[CH2:30][C:29]2[NH:1][C:2]3[CH2:6][CH2:5][C:4](=[O:7])[C:3]=3[CH:12]([C:11]3[CH:14]=[CH:15][C:16]([F:17])=[C:9]([Br:8])[CH:10]=3)[C:28]=2[C:27](=[O:32])[CH2:26]1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

참가 물질

5

반응물 3

HCID 1736043-Bromo-4-fluorobenzaldehydeHCID 111381741-Benzylpiperidine-3,5-dioneHCID 122914403-Aminocyclopent-2-en-1-one

생성물 1

HCID 113288132-benzyl-5-(3-bromo-4-fluorophenyl)-2,3,5,7,8,9-hexahydro-1H-cyclopenta[b][1,7]naphthyridine-4,6-dione수율 64.2%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of 3-amino-2-cyclopenten-1-one (Kikani, B. B., Synthesis, (1991), 2, 176) (0.97 g, 10 mmol), 3-bromo-4-fluorobenzaldehyde (2.0 g, 10 mmol) and N-benzylpiperidine-3,5-dione (Ziegler, J. Amer. Chem. Soc. (1973), 95, 7458-7464) (2.2 g, 10 mmol) in ethyl alcohol (10 mL) was heated to reflux for 72 hours and then allowed to cool to ambient temperature. The solvent was evaporated and the residue was purified by flash chromatography over silica gel (5% ethanol/methylene chloride) to provide the title compound (3.0 g).

후처리

  1. temperatureto reflux for 72 hours
  2. customThe solvent was evaporated
  3. customthe residue was purified by flash chromatography over silica gel (5% ethanol/methylene chloride)

출처 및 근거

ORD 기록
ord-58f8bb02fe4a456fbc8ac123f7d0819e
출처 데이터셋
uspto-grants-2001_02
특허 번호
US06191140B1

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