5'-Fluoro-5-nitro-3,3'-bipyridin-4-amine → 5'-Fluoro-3,3'-bipyridine-4,5-diamine

HRID 334481ノート

反応式

HRID 334481 の反応式
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[N:10][CH:11]=[C:12]([N+:15]([O-])=O)[C:13]=2[NH2:14])[CH:5]=[N:6][CH:7]=1>CCO.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[N:10][CH:11]=[C:12]([NH2:15])[C:13]=2[NH2:14])[CH:5]=[N:6][CH:7]=1

参加物

4

反応物 1

HCID 867010655'-Fluoro-5-nitro-3,3'-bipyridin-4-amine

生成物 1

HCID 867010665'-Fluoro-3,3'-bipyridine-4,5-diamine収率 100%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

To a solution of 5′-fluoro-5-nitro-3,3′-bipyridin-4-amine (LXXI) (621 mg, 2.65 mmol) in EtOH (18 mL) was added 10% Pd/C (93 mg, 15% by wt). The solution was purged with hydrogen and stirred for overnight at room temperature under hydrogen. The suspension was filtered through Celite and concentrated under vacuum. The crude product was purified through a silica gel column (100% CHCl3→3:97 MeOH[7N NH3]:CHCl3) to produce 5′-fluoro-3,3′-bipyridine-4,5-diamine (LXXII) as an off-white solid (542 mg, 2.65 mmol, 100% yield). 1H NMR (DMSO-d6, 500 MHz) δ ppm 4.78 (brs, 2H), 5.28 (brs, 2H), 7.46 (s, 1H), 7.70 (s, 1H), 7.73-7.76 (m, 1H), 8.44-8.45 (m, 1H), 8.56 (d, J=2.8 Hz, 1H); ESIMS found C10H9FN4 m/z 205 (M+H).

後処理

  1. customThe solution was purged with hydrogen
  2. filtrationThe suspension was filtered through Celite
  3. concentrationconcentrated under vacuum
  4. customThe crude product was purified through a silica gel column (100% CHCl3→3:97 MeOH[7N NH3]:CHCl3)

出典と根拠

ORDレコード
ord-09c82c58e3e54b108df5c9249444259e
出典データセット
uspto-grants-2014_11
特許番号
US08883822B2

反応ノート

読み込み中…