Cesium carbonate → Tert-butyl 2-{4-[(6-nitro-3-pyridinyl)oxy]benzoyl}hydrazinecarboxylate

HRID 606329노트

반응식

HRID 606329 반응식
[OH:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([NH:8][NH:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:7])=[CH:4][CH:3]=1.Br[C:20]1[CH:21]=[CH:22][C:23]([N+:26]([O-:28])=[O:27])=[N:24][CH:25]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[N+:26]([C:23]1[N:24]=[CH:25][C:20]([O:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([NH:8][NH:9][C:10]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:11])=[O:7])=[CH:17][CH:18]=2)=[CH:21][CH:22]=1)([O-:28])=[O:27]

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 8176205-Bromo-2-nitropyridineHCID 9813709HCID 9813709, 화합물

생성물 1

HCID 59686995Tert-butyl 2-{4-[(6-nitro-3-pyridinyl)oxy]benzoyl}hydrazinecarboxylate수율 72%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

To a mixture of tert-butyl 2-(4-hydroxybenzoyl)hydrazinecarboxylate (0.688 g, 2.73 mmol) and 5-bromo-2-nitropyridine (0.554 mg, 2.73 mmol) and caesium carbonate (1.33 g, 4.08 mmol) in N,N-dimethylformamide (7 mL) was stirred overnight at 80° C. The solution was concentrated and the residue was taken with dichloromethane and water. The organic phase was dried on MgSO4 and concentrated. The crude product was purified by column chromatography (silica gel, 5% MeOH in CH2Cl2), to give 736 mg of the mixture nitropyridine and bromopyridine.

후처리

  1. concentrationThe solution was concentrated
  2. customThe organic phase was dried on MgSO4
  3. concentrationconcentrated
  4. customThe crude product was purified by column chromatography (silica gel, 5% MeOH in CH2Cl2)

출처 및 근거

ORD 기록
ord-200ee54e449e4610bf3e3c13b02cbcbe
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915295B2

반응 노트

불러오는 중…