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tert-Butyl methacrylate → HCID 66839446, compound

HRID 546745
Notes
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Reaction equation

HRID 546745 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([N:10]2[CH:14]=[C:13]([CH3:15])[N:12]=[CH:11]2)=[CH:4][CH:3]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C([O-])(=O)C.[Na+].[C:43]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])(=[O:47])[C:44]([CH3:46])=[CH2:45]>[CH2-]C=C.[CH2-]C=C.Cl[Pd+].Cl[Pd+].C1(C)C=CC=CC=1.CC(N(C)C)=O>[CH3:9][O:8][C:6]1[N:7]=[C:2](/[CH:45]=[C:44](\[CH3:46])/[C:43]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[CH:3]=[CH:4][C:5]=1[N:10]1[CH:14]=[C:13]([CH3:15])[N:12]=[CH:11]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 11448tert-Butyl methacrylateHCID 80271Tri-o-tolylphosphineHCID 517045Sodium AcetateHCID 86628513HCID 86628513, compound

Product 1

HCID 66839446HCID 66839446, compound

Reagents, catalysts & solvents 3

HCID 61538
Palladium, di-mu-chlorobis(eta3-2-propenyl)di-
Catalyst
HCID 1140TolueneSolvent
HCID 31374DimethylacetamideSolvent

Procedure

A mixture of 6-chloro-2-methoxy-3-(4-methyl-1H-imidazol-1-yl)pyridine (400 mg), an allylpalladium chloride dimer (32.8 mg), tri-o-tolylphosphine (54.4 mg), sodium acetate (441 mg), dimethylacetamide (0.640 mL), tert-butyl methacrylate (0.724 mL) and toluene (2 mL) was stirred in a nitrogen atmosphere at 120° C. for 3.5 hours. The reaction solution was left to cool to room temperature. Then, a silica gel was added and the reaction solution was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system) to obtain 313 mg of tert-butyl (E)-3-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]-2-methylacrylate. The ester was diluted with trifluoroacetic acid (2.48 mL) and methylene chloride (2.48 mL), and the reaction solution was stirred at room temperature for 3.5 hours. The reaction solution was concentrated under reduced pressure to obtain 260 mg of the title compound. The property value of the compound is as follows.

Workup

  1. waitThe reaction solution was left
  2. additionThen, a silica gel was added
  3. concentrationthe reaction solution was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system)

Sources & evidence

ORD record
ord-1a6ccff7f5344086a8c634df1131230c
Source dataset
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07935815B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes