Ethyl Bromide → HCID 69275411, compound

HRID 2375390Notes

Reaction equation

HRID 2375390 reaction equation
[C:1]([C:4]1[C:5]([C:19](=[O:21])[CH3:20])=[C:6]([CH3:18])[N:7]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([Cl:17])[CH:11]=2)[C:8]=1[CH3:9])(=[O:3])[CH3:2].Br[CH2:23][CH3:24].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:1]([C:4]1[C:5]([C:19](=[O:21])[CH3:20])=[C:6]([CH3:18])[N:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:23][CH3:24])=[C:12]([Cl:17])[CH:11]=2)[C:8]=1[CH3:9])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 69275407HCID 69275407, compound

Product 1

HCID 69275411HCID 69275411, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 1-[4-acetyl-1-(3-chloro-4-hydroxy-phenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-ethanone (prepared as outline in Example 57; 80 mg, 0.27 mmol) in 3 mL of dry DMF was added bromoethane (54 mg, 0.5 mmol) and K2CO3 powder (50 mg). The resulting reaction mixture was warmed to 50° C. and stirred for 1 h. It was quenched by addition of 20 mL of H2O, extracted with diethyl ether (20 mL×2). The combined organic extracts were washed with brine (50 mL), dried (MgSO4), filtered, and concentrated in vacuo to afford 1-[4-acetyl-1-(3-chloro-4-ethoxy-phenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-ethanone: MS (ESI) 302 (M+H)+.

Workup

  1. customThe resulting reaction mixture
  2. customIt was quenched by addition of 20 mL of H2O
  3. extractionextracted with diethyl ether (20 mL×2)
  4. washThe combined organic extracts were washed with brine (50 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-722229670e5b4e2592682c0901d61356
Source dataset
uspto-grants-2008_12
Patent number
US07465730B2

Reaction notes

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