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Potassium Carbonate → HCID 22030186, compound

HRID 968617
Notes
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Reaction equation

HRID 968617 reaction equation
Cl[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][N:15]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.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>[CH3:12][O:13][C:14]1[N:15]=[CH:16][C:17]([C:2]2[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:18][CH:19]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 5898332-Chloro-3-(trifluoromethyl)pyridineHCID 2734368(6-Methoxypyridin-3-yl)boronic acid

Product 1

HCID 22030186HCID 22030186, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst
HCID 1140TolueneSolvent

Procedure

Heat a mixture of 2-chloro-3-trifluoromethylpyridine (37 g, 0.2 mol), 2-methoxypyridine-5-boronic acid (32 g, 0.21 mol), tetrakis(triphenylphosphine)palladium(0) (9 g, 7 mmol) and 2M potassium carbonate (150 mL) in toluene (500 mL) under a nitrogen atmosphere at 90° C. for 8 hours. Cool the reaction mixture and separate the layers. Extract the aqueous layer with ethyl acetate (2×250 mL) and wash the combined organics with 4M sodium hydroxide (250 mL), water (250 mL), and brine (250 mL). Dry (MgSO4) and concentrate under reduced pressure. Purify the resulting oil by flash chromatography on silica gel (50% ether/50% hexane) to give the title compound (48.2 g, 95%) as a colorless oil.

Workup

  1. temperatureHeat
  2. temperatureCool the reaction mixture
  3. customseparate the layers
  4. extractionExtract the aqueous layer with ethyl acetate (2×250 mL)
  5. washwash the combined organics with 4M sodium hydroxide (250 mL), water (250 mL), and brine (250 mL)
  6. dry with materialDry (MgSO4)
  7. concentrationconcentrate under reduced pressure
  8. customPurify the resulting oil by flash chromatography on silica gel (50% ether/50% hexane)

Sources & evidence

ORD record
ord-86cb2a80c7bf4fce84f6c238e81151c2
Source dataset
uspto-grants-2007_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07304059B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes