Methyl iodide → HCID 58259902, compound

HRID 1020210Notes

Reaction equation

HRID 1020210 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][NH:12][C:11](=[O:18])[CH:10]=2)=[C:4]([F:19])[CH:3]=1.[H-].[Na+].[CH3:22]I>CN(C=O)C>[F:19][C:4]1[CH:3]=[C:2]([Br:1])[CH:7]=[CH:6][C:5]=1[NH:8][C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][N:12]([CH3:22])[C:11](=[O:18])[CH:10]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 574382734-[(4-Bromo-2-fluorophenyl)amino]-5-nitro-2(1H)-pyridinone

Product 1

HCID 58259902HCID 58259902, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the yellow solution of 4-(4-bromo-2-fluorophenylamino)-5-nitropyridin-2(1H)-one (1.235 g, 3.78 mmol) dissolved in dry DMF (15 mL) at −5−>0° C., was added NaH (182 mg, 4.55 mmol) (60% in oil). The color of solution turned into dark brown in 20 min at 0° C. The stirring was continued at r.t. for 40 minutes, followed by the addition of MeI (283 uL, 4.54 mmol) through a syringe at 5° C. The resulted solution was stirred at r.t. for 36 hours. The desired compound started to precipitate out of solution after 20 min of MeI addition. Water was added, and the precipitate was vacuum filtered, washed with water, and dried at 40° C. under a high vacuum for 2.5 hours. The product was used for the next reaction without further purification. (1.12 gram, 87% yield).

Workup

  1. customdark brown in 20 min
  2. customat 0° C

Sources & evidence

ORD record
ord-f76f3676a1f04b85bf85b593859b642c
Source dataset
uspto-grants-2014_05
Patent number
US08716318B2

Reaction notes

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