Dimethylformamide → HCID 117839581, compound

HRID 1477657Notes

Reaction equation

HRID 1477657 reaction equation
[CH3:1]N(C)C=O.[F:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[NH:14][CH:15]=[C:16]([N+:18]([O-:20])=[O:19])[CH:17]=2)=[CH:9][CH:8]=1.[H-].[Na+].CI>C1(C)C=CC=CC=1.O>[F:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[N:14]([CH3:1])[CH:15]=[C:16]([N+:18]([O-:20])=[O:19])[CH:17]=2)=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 117839453HCID 117839453, compound

Product 1

HCID 117839581HCID 117839581, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To an N,N-dimethylformamide solution (0.50 mL) of 2-(4-fluorophenyl)-4-nitro-1H-pyrrole (10.0 mg, 0.0485 mmol) synthesized in Reference Synthesis Example 245, sodium hydride (2.50 mg, 0.0582 mmol) was added at 0° C. and the resultant mixture was stirred for 1 hour. Thereafter, methyl iodide (18.8 μL, 0.0582 mmol) was added to the reaction solution and the resultant mixture was stirred at room temperature for 7 hours and 30 minutes. After completion of the reaction, water was added to the reaction solution and extraction from the resultant mixture with toluene was performed. The organic layer was concentrated under reduced pressure to obtain the title compound as a crude product.

Workup

  1. additionwas added at 0° C.
  2. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f0d9a4fac2284737bdb039b4b0faeb19
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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