Allyl bromide → HCID 58763935, compound

HRID 859184Notes

Reaction equation

HRID 859184 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6]([C:8]1[C:12]([OH:13])=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[N:10]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[Cl:27])[N:9]=1)=[O:7])[CH3:4].[CH2:28](Br)[CH:29]=[CH2:30].C(OCC)(=O)C>CS(C)=O>[CH2:3]([O:5][C:6]([C:8]1[C:12]([O:13][CH2:30][CH:29]=[CH2:28])=[C:11]([C:14]2[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=2)[N:10]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[Cl:27])[N:9]=1)=[O:7])[CH3:4]

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 24828929HCID 24828929, compound

Product 1

HCID 58763935HCID 58763935, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a slurry of sodium hydride (39 mg of 60% in oil) in DMSO (2.4 ml) was added 5-(4-chlorophenyl)-1-(2-chlorophenyl)-4-hydroxy-1H-pyrazole-3-carboxylic acid ethyl ester I-1d (300 mg, 0.8 mmol) and the mixture was agitated for 45 minutes. Allyl bromide (0.1 ml, 1.2 mmol) was added and stirring was continued for 4.5 hours. The reaction solution was diluted into ethyl acetate, washed with water (2×), brine, dried (Na2SO4) and concentrated in vacuo to afford the title compound (I-1e) as an orange oil, 340 mg. This material was taken onto the next step without further purification.

Workup

  1. stirringstirring
  2. waitwas continued for 4.5 hours
  3. washwashed with water (2×), brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-00aa5c030d9e423fbee44a1e4c42cfdf
Source dataset
uspto-grants-2006_12
Patent number
US07151097B2

Reaction notes

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