1,6-Naphthyridine → 1,2,3,4-Tetrahydro-1,8-naphthyridine

HRID 1861682ノート

反応式

HRID 1861682 の反応式
[N:1]1[C:10]2[C:5](=[CH:6][N:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1>CCO.[Pd]>[NH:1]1[C:6]2[C:5](=[CH:10][CH:9]=[CH:8][N:7]=2)[CH2:4][CH2:3][CH2:2]1

参加物

4

反応物 1

HCID 674881,6-Naphthyridine

生成物 1

HCID 130473671,2,3,4-Tetrahydro-1,8-naphthyridine

試薬・触媒・溶媒 2

HCID 23938Palladium触媒2 回HCID 702Ethanol溶媒2 回

実験手順

To a solution of 0.8315 g (6.39 mmol) 1,6-naphthyridine in 25 mL EtOH was added 0.0875 g Pd (10% on C). The reaction mixture was stirred under H2 at atmospheric pressure. After 24 h, an additional 0.0431 g Pd (10% on C) was added. After a total of 46 h under H2 at atmospheric pressure, the reaction mixture was diluted with 50 mL EtOH and filtered over celite. The celite was washed with 300 mL EtOH, and the filtrate concentrated in vacuo. Purification by flash chromatography (50×105 mm silica gel, linear gradient 5-10% (10% NH4H:MeOH):CH2Cl2) yielded 32. 1H NMR (CDCl3, 400 MHz) δ 7.969 (d, 2H, J=4.94 Hz, ArH); 6.279 (d, 1H, J=5.57 Hz, ArH); 3.361-3.326 (m, 2H, CH2); 2.703 (t, 2H, J=6.27 Hz, CH2); 1.962-1.903 (m, 2H, CH2); MS (Electrospray): m/z 134.9 (M+H).

後処理

  1. filtrationfiltered over celite
  2. washThe celite was washed with 300 mL EtOH
  3. concentrationthe filtrate concentrated in vacuo
  4. customPurification by flash chromatography (50×105 mm silica gel, linear gradient 5-10% (10% NH4H:MeOH):CH2Cl2)

出典と根拠

ORDレコード
ord-21a926f21800491e96d0358057b29099
出典データセット
uspto-grants-2003_03
特許番号
US06534510B2

反応ノート

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