p-Fluoronitrobenzene → HCID 69332311, compound

HRID 2370929Notes

Reaction equation

HRID 2370929 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[N:14]=[CH:13][C:12]([CH2:15][C:16]([C:25]2[N:26]=[CH:27][NH:28][CH:29]=2)([C:21]([O:23][CH3:24])=[O:22])[C:17]([O:19][CH3:20])=[O:18])=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].F[C:33]1[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=1.C([O-])(O)=O.[Na+]>CN(C=O)C>[C:1]([O:5][C:6]([NH:8][C:9]1[N:14]=[CH:13][C:12]([CH2:15][C:16]([C:25]2[N:26]=[CH:27][N:28]([C:33]3[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=3)[CH:29]=2)([C:21]([O:23][CH3:24])=[O:22])[C:17]([O:19][CH3:20])=[O:18])=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 178499928HCID 178499928, compound

Product 1

HCID 69332311HCID 69332311, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 404 mg (1.00 mmol) of the compound from example 12d in 10 ml of DMF was cooled to 0° C. and, while stirring, 80 mg (2.00 mmol, 60%) of sodium hydride were added in portions. The mixture was stirred at 0° C. for 1 h and then 423 mg (3 mmol) of 4-fluoronitrobenzene were added and stirred at RT until conversion was complete. Saturated aqueous NaHCO3 solution was added to the mixture, which was extracted with EA. The organic phase was dried over Na2SO4, filtered and concentrated. The residue was purified by chromatography on silica gel. 394 mg of the title compound were obtained.

Workup

  1. stirringThe mixture was stirred at 0° C. for 1 h
  2. stirringstirred at RT until conversion
  3. extractionwas extracted with EA
  4. dry with materialThe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-7e14014b3c2c4b67ae420f1ff0923569
Source dataset
uspto-grants-2014_04
Patent number
US08710232B2

Reaction notes

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