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Potassium Carbonate → HCID 57683752, compound

HRID 1664091
Notes
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Reaction equation

HRID 1664091 reaction equation
I[C:2]1[CH:7]=[C:6]([N:8]([CH3:10])[CH3:9])[CH:5]=[CH:4][N:3]=1.[CH3:11][O:12][C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][CH:18]=1.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:11][O:12][C:13]1[CH:18]=[C:17]([C:2]2[CH:7]=[C:6]([N:8]([CH3:10])[CH3:9])[CH:5]=[CH:4][N:3]=2)[CH:16]=[CH:15][CH:14]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 2734370(3-Methoxyphenyl)boronic acidHCID 110861002-Iodo-4-dimethylaminopyridine

Product 1

HCID 57683752HCID 57683752, compoundYield 84%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalyst
HCID 962
Water
Solvent
HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-iodo-4-dimethylaminopyridine (2.7 g, 11 mmol), 3-methoxyphenylboronic acid (2 g, 13 mmol) and K2CO3 (5.4 g, 39 mmol) in toluene (60 ml) and water (10 ml) were degased with nitrogen for 15 minutes. Pd(PPh3)4 (800 mg, 0.66 mmol) was added and the resulting mixture was heated to 90° C. for 48 hours under nitrogen. After being cooled to room temperature, the aqueous phase was separated and extracted with EtOAc (3×100 ml). The combined organic fractions were washed with brine, dried over MgSO4, filtered and evaporated. The crude compound was purified by column chromatography (SiO2, EtOAc) to afford 2.1 g (84%) of the titled compound as a colorless oil, which solidify upon standing. If some impurities remains, the compound can be purified by following the acidic extraction followed by basic recovery as performed before for 2-phenyl-4-dimethylaminopyridine.

Workup

  1. customwere degased with nitrogen for 15 minutes
  2. temperatureAfter being cooled to room temperature
  3. customthe aqueous phase was separated
  4. extractionextracted with EtOAc (3×100 ml)
  5. washThe combined organic fractions were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude compound was purified by column chromatography (SiO2, EtOAc)

Sources & evidence

ORD record
ord-70b6999d0c934b06a85b3d9de2921893
Source dataset
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08039124B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes