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Potassium Carbonate → 3-butoxy-4'-[2-(2,6-dichloro-phenyl)-4-isopropyl-2H-pyrazol-3-ylmethoxy]-2'-methyl-biphenyl-4-carbaldehyde

HRID 2261863
Notes
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Reaction equation

HRID 2261863 reaction equation
[CH2:1]([O:5][C:6]1[CH:7]=[C:8]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][C:15]=2[CH3:21])[CH:9]=[CH:10][C:11]=1[CH:12]=[O:13])[CH2:2][CH2:3][CH3:4].Br[CH2:23][C:24]1[N:28]([C:29]2[C:34]([Cl:35])=[CH:33][CH:32]=[CH:31][C:30]=2[Cl:36])[N:27]=[CH:26][C:25]=1[CH:37]([CH3:39])[CH3:38].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:1]([O:5][C:6]1[CH:7]=[C:8]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:23][C:24]3[N:28]([C:29]4[C:34]([Cl:35])=[CH:33][CH:32]=[CH:31][C:30]=4[Cl:36])[N:27]=[CH:26][C:25]=3[CH:37]([CH3:39])[CH3:38])=[CH:16][C:15]=2[CH3:21])[CH:9]=[CH:10][C:11]=1[CH:12]=[O:13])[CH2:2][CH2:3][CH3:4]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 574433665-Bromomethyl-1-(2,6-dichlorophenyl)-4-isopropyl-1H-pyrazoleHCID 866354693-Butoxy-4'-hydroxy-2'-methyl-biphenyl-4-carbaldehyde

Product 1

HCID 866354713-butoxy-4'-[2-(2,6-dichloro-phenyl)-4-isopropyl-2H-pyrazol-3-ylmethoxy]-2'-methyl-biphenyl-4-carbaldehydeYield 33%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
70 °C

Procedure

A solution of 3-butoxy-4′-hydroxy-2′-methyl-biphenyl-4-carbaldehyde (0.198 g, 0.696 mmol) and 5-bromomethyl-4-isopropyl-1-(2,6-dichloro-phenyl)-1H-pyrazole (0.242 g, 0.696 mmol) in DMF (2.0 mL) is treated with K2CO3 (0.192 g, 1.39 mmol). The mixture is stirred at 70° C. for 2 hours. The mixture is cooled to room temperature and quenched with water (10 mL). The mixture is extracted with ethyl acetate (20 mL×2), and the combined organic layers are dried over sodium sulfate and concentrated under reduced pressure. The residue is purified by silica gel chromatography eluting with 20% ethyl acetate in hexanes to give 3-butoxy-4′-[2-(2,6-dichloro-phenyl)-4-isopropyl-2H-pyrazol-3-ylmethoxy]-2′-methyl-biphenyl-4-carbaldehyde (0.125 g, 33%). ES/MS m/e 551.0; 553.0 (M+1).

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. customquenched with water (10 mL)
  3. extractionThe mixture is extracted with ethyl acetate (20 mL×2)
  4. dry with materialthe combined organic layers are dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by silica gel chromatography
  7. washeluting with 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-ffafba6935934e6f8e05f0f44dc6e040
Source dataset
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07846960B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes