p-Fluoronitrobenzene → HCID 131727547, compound

HRID 230752Notes

Reaction equation

HRID 230752 reaction equation
[NH:1]1[C:9]2[CH:8]=[C:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[N:6]=[CH:5][C:4]=2[CH:3]=[CH:2]1.[H-].[Na+].F[C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=1>CN(C=O)C>[N+:26]([C:23]1[CH:24]=[CH:25][C:20]([N:1]2[C:5]3[N:6]=[C:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:8]=[CH:9][C:4]=3[CH:3]=[CH:2]2)=[CH:21][CH:22]=1)([O-:28])=[O:27]

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydrideHCID 57763153HCID 57763153, compound

Product 1

HCID 131727547HCID 131727547, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl 1H-pyrrolo[3,2-c]pyridine-6-carboxylate (120 mg, 0.55 mmol) in DMF (3 mL) at rt, was added NaH (60% in mineral oil, 26.4 mg, 0.66 mmol). The mixture was stirred for 10 min and 4-fluoronitrobenzene (155 mg, 1.1 mmol) was added to the reaction. The resulting mixture was stirred at rt for 1 h. The reaction was quenched with sat. aq. sodium citrate solution, extracted with EtOAc and dried over MgSO4. The product was purified by flash column chromatography (SiO2, 25% EtOAc/CH2Cl2) to give a yellow solid (137 mg, 73%).

Workup

  1. stirringThe resulting mixture was stirred at rt for 1 h
  2. customThe reaction was quenched with sat. aq. sodium citrate solution
  3. extractionextracted with EtOAc
  4. dry with materialdried over MgSO4
  5. customThe product was purified by flash column chromatography (SiO2, 25% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-4ce45011fdc541b498ab221deab2ca37
Source dataset
uspto-grants-2009_07
Patent number
US07566784B2

Reaction notes

Loading…