1,2-Dibromoethane → 1-(1-(2-Bromoethyl)-3-(2,5-dimethyl-1H-pyrrol-1-yl)-1H-pyrazol-5-yl)ethanone

HRID 407785Notes

Reaction equation

HRID 407785 reaction equation
[CH3:1][C:2]1[N:3]([C:8]2[CH:12]=[C:11]([C:13](=[O:15])[CH3:14])[NH:10][N:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1.[Br:16][CH2:17][CH2:18]Br.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[Br:16][CH2:17][CH2:18][N:10]1[C:11]([C:13](=[O:15])[CH3:14])=[CH:12][C:8]([N:3]2[C:2]([CH3:1])=[CH:6][CH:5]=[C:4]2[CH3:7])=[N:9]1

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 866840471-(3-(2,5-Dimethyl-1H-pyrrol-1-yl)-1H-pyrazol-5-yl)ethanone

Product 1

HCID 866840481-(1-(2-Bromoethyl)-3-(2,5-dimethyl-1H-pyrrol-1-yl)-1H-pyrazol-5-yl)ethanoneYield 91%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A 250-mL round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 150d (5.4 g, 1.0 eq., 26.6 mmol), 1,2-dibromoethane (20.0 g, 4.0 eq., 106.4 mmol), K2CO3 (7.34 g, 2.0 eq., 53.2 mmol), and acetonitrile (100 mL). The reaction mixture was reflux for 5 hrs. It was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with 6:1 petroleum ether/ethyl acetate to afford 150e (7.5 g, 91%) as a colorless oil. MS-ESI: [M+H]+ 309.9

Workup

  1. customA 250-mL round-bottomed flask equipped with a magnetic stirrer and a reflux condenser
  2. temperatureThe reaction mixture was reflux for 5 hrs
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica-gel column chromatography
  6. washeluting with 6:1 petroleum ether/ethyl acetate

Sources & evidence

ORD record
ord-a7364230d3514fa68f2c61d162ce5c6e
Source dataset
uspto-grants-2014_06
Patent number
US08754077B2

Reaction notes

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