Water → HCID 58305731, compound

HRID 2280327Notes

Reaction equation

HRID 2280327 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N:11]1[CH:15]=[CH:14][CH:13]=[CH:12]1)[C:5]([NH2:7])=O.[Br:16]N1C(=O)CCC1=O.O>CN(C=O)C>[Br:16][C:12]1[N:11]([C:10]2[CH:9]=[CH:8][C:4]([C:5]#[N:7])=[CH:3][C:2]=2[CH3:1])[CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 58305652HCID 58305652, compound

Product 1

HCID 58305731HCID 58305731, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-methyl-4-(1H-pyrrol-1-yl)benzamide (6A, see first step of Scheme 6 for synthesis) in DMF (5 mL) was added N-bromosuccinimide (177 mg, 1 mmol) portionwise at 0° C., after the addition was completed, the mixture was stirred at room temperature for 35 min. The reaction mixture was poured into water, and extracted with ethyl acetate (10 mL×3). The combined organic layers were washed with brine (25 mL×2), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate=5:1) to afford 50B (100 mg, yield 36%).

Workup

  1. additionafter the addition
  2. extractionextracted with ethyl acetate (10 mL×3)
  3. washThe combined organic layers were washed with brine (25 mL×2)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate=5:1)

Sources & evidence

ORD record
ord-8e67558184f649d1a4cefe6b93883c8c
Source dataset
uspto-grants-2015_09
Patent number
US09138427B2

Reaction notes

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