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

HRID 589461노트

반응식

HRID 589461 반응식
[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

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-f424f380c502418e8413078de9661f4d
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09233104B2

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