4-Methyl-5-[[2-(1-methyl-1h-pyrazol-4-yl)-4-pyridinyl]oxy]-2-nitropyridine → 4-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-amine

HRID 1049250노트

반응식

HRID 1049250 반응식
[CH3:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([C:15]3[CH:16]=[N:17][N:18]([CH3:20])[CH:19]=3)[CH:10]=2)=[CH:6][N:5]=[C:4]([N+:21]([O-])=O)[CH:3]=1>CCOC(C)=O.[Pd]>[CH3:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([C:15]3[CH:16]=[N:17][N:18]([CH3:20])[CH:19]=3)[CH:10]=2)=[CH:6][N:5]=[C:4]([NH2:21])[CH:3]=1

참가 물질

4

반응물 1

HCID 904033434-Methyl-5-[[2-(1-methyl-1h-pyrazol-4-yl)-4-pyridinyl]oxy]-2-nitropyridine

생성물 1

HCID 686640964-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-amine수율 100%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 4-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)-2-nitropyridine (0.83 g, 2.67 mmol) in EtOAc (20 mL) was treated with palladium on carbon (50% wet, 0.284 g, 0.267 mmol) and hydrogenated (1 atm) overnight. The solids were removed via filtration through diatomaceous earth, rinsed well with EtOAc and the filtrate was concentrated to dryness to afford crude 4-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-amine (750 mg, 100%) as a white amorphous solid which was carried on to the next step without further purification. 1H NMR (400 MHz, DMSO-d6): δ 8.30 (d, J=5.7 Hz, 1H), 8.23 (s, 1H), 7.93 (d, J=0.7 Hz, 1H), 7.69 (s, 1H), 7.12 (d, J=2.4 Hz, 1H), 6.51 (dd, J=5.7, 2.4 Hz, 1H), 6.39 (s, 1H), 5.91 (s, 2H), 3.84 (s, 3H), 1.95 (s, 3H); MS (ESI) m/z: 282.1 (M+H+).

후처리

  1. customThe solids were removed via filtration through diatomaceous earth
  2. washrinsed well with EtOAc
  3. concentrationthe filtrate was concentrated to dryness

출처 및 근거

ORD 기록
ord-858acb6d14074a1bb9da017b6a4c5e2b
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09382228B2

반응 노트

불러오는 중…