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

HRID 606329ノート

反応式

HRID 606329 の反応式
[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]

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 8176205-Bromo-2-nitropyridineHCID 9813709HCID 9813709、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-200ee54e449e4610bf3e3c13b02cbcbe
出典データセット
uspto-grants-2011_03
特許番号
US07915295B2

反応ノート

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