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

HRID 606329Notes

Reaction equation

HRID 606329 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-200ee54e449e4610bf3e3c13b02cbcbe
Source dataset
uspto-grants-2011_03
Patent number
US07915295B2

Reaction notes

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