Methyl 2-benzyl-9-bromo-5-oxo-1,2,3,4,5,10-hexahydrobenzo[b][1,7]naphthyridine-6-carboxylate → Methyl 2-benzyl-5-oxo-1,2,3,4,5,10-hexahydrobenzo[b][1,7]naphthyridine-6-carboxylate

HRID 521427

反応式

HRID 521427 の反応式
[CH2:1]([N:8]1[CH2:17][C:16]2[NH:15][C:14]3[C:18](Br)=[CH:19][CH:20]=[C:21]([C:22]([O:24][CH3:25])=[O:23])[C:13]=3[C:12](=[O:27])[C:11]=2[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>CO.[Pd]>[CH2:1]([N:8]1[CH2:17][C:16]2[NH:15][C:14]3[CH:18]=[CH:19][CH:20]=[C:21]([C:22]([O:24][CH3:25])=[O:23])[C:13]=3[C:12](=[O:27])[C:11]=2[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 2

HCID 89657401Methyl 2-benzyl-9-bromo-5-oxo-1,2,3,4,5,10-hexahydrobenzo[b][1,7]naphthyridine-6-carboxylateHCID 178418361HCID 178418361、化合物

生成物 1

HCID 121297550Methyl 2-benzyl-5-oxo-1,2,3,4,5,10-hexahydrobenzo[b][1,7]naphthyridine-6-carboxylate収率 62.4%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

To a solution of methyl 2-benzyl-9-bromo-5-oxo-1,2,3,4,5,10-hexahydrobenzo[b][1,7]naphthyridine-6-carboxylate (0.1 g, 0.23 mmol) in MeOH (3 mL) was added Pd/C (0.04 g, 5%, 50% water), and the mixture was stirred at atmosphere of hydrogen for about 2.5 h. Debromination occurred without substantially removing benzyl group under this condition. Then the mixture was filtered, washed with MeOH (50 mL), concentrated and was chromatographed on silica gel to afford the product (0.05 g). MS (ESI) m/e [M+1]+ 349.0.

後処理

  1. filtrationThen the mixture was filtered
  2. washwashed with MeOH (50 mL)
  3. concentrationconcentrated
  4. customwas chromatographed on silica gel

出典と根拠

ORDレコード
ord-7c0fa855a02548d2bb2bdab4f0453e03
出典データセット
uspto-grants-2016_05
特許番号
US09328111B2

関連ノート

読み込み中…