p-Fluoronitrobenzene → HCID 59189900, compound

HRID 216616Notes

Reaction equation

HRID 216616 reaction equation
[NH2:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[C:11]([NH2:13])=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2.F[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1.[H-].[Na+]>CN(C)C=O>[NH2:1][C:2]1[N:3]([C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)[C:4]2[C:9]([C:10]=1[C:11]([NH2:13])=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydrideHCID 21862598HCID 21862598, compound2×

Product 1

HCID 59189900HCID 59189900, compoundYield 26.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
85 °C

Procedure

A solution of 2-aminoindole-3-carboxamide (Reference compound 18-1, 0.20 g, 1.1 mmol) in anhydrous N,N-dimethylformamide (2 mL) and a solution of 4-fluoronitrobenzene (0.13 mL, 1.3 mmol) in anhydrous N,N-dimethylformamide (2 mL) were successively added to a suspension of sodium hydride (purity 60%, g, 1.3 mmol) in anhydrous N,N-dimethylformamide (3 mL) under ice-cooling, and the mixture was stirred at 85° C. for 3 hours. The reaction mixture was poured into ice-water (20 mL), the precipitated solid was washed with ethyl acetate (4 mL). The resultant solid was dried under reduced pressure to give the title reference compound (0.087 g) as a brown solid (yield 26%).

Workup

  1. temperaturecooling
  2. washthe precipitated solid was washed with ethyl acetate (4 mL)
  3. customThe resultant solid was dried under reduced pressure

Sources & evidence

ORD record
ord-9b8d91be799442fe91b4880ebe2286e8
Source dataset
uspto-grants-2012_06
Patent number
US08193237B2

Reaction notes

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