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 478261ノート

反応式

HRID 478261 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-7de4d39e05de4fbaa8cd757701196d42
出典データセット
uspto-grants-2003_11
特許番号
US06642222B2

反応ノート

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