Tert-butyl {2-chloro-5-[(6-nitropyridin-3-yl)oxy]phenyl}carbamate → Tert-butyl {5-[(6-aminopyridin-3-yl)oxy]-2-chlorophenyl}carbamate

HRID 1874373

반응식

HRID 1874373 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:10]=[N:11][C:12]([N+:15]([O-])=O)=[CH:13][CH:14]=2)=[CH:4][C:3]=1[NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22]>CO.[C].[Pd]>[NH2:15][C:12]1[N:11]=[CH:10][C:9]([O:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH:4]=2)=[CH:14][CH:13]=1

참가 물질

4

반응물 1

HCID 57749305Tert-butyl {2-chloro-5-[(6-nitropyridin-3-yl)oxy]phenyl}carbamate

생성물 1

HCID 57749356Tert-butyl {5-[(6-aminopyridin-3-yl)oxy]-2-chlorophenyl}carbamate수율 59%

시약·촉매·용매 2

HCID 178418390HCID 178418390, 화합물촉매HCID 887Methanol용매

실험 절차

To a solution of tert-butyl {2-chloro-5-[(6-nitropyridin-3-yl)oxy]phenyl}carbamate (13.5 g, 36.9 mmol) in methanol (500 mL) was added palladium carbon (50% water-containing product, 2.96 g), and the mixture was stirred under a hydrogen atmosphere at room temperature for 17 hr. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, hexane/ethyl acetate=100/0→75/25) to give the title compound (7.29 g, 59%) as a pale-yellow oil.

후처리

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by column chromatography (silica gel, hexane/ethyl acetate=100/0→75/25)

출처 및 근거

ORD 기록
ord-2b3c2fcb0a664a5badbe9d02c0b9e86c
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304557B2

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