Potassium Carbonate → HCID 69041910, compound

HRID 433601Notes

Reaction equation

HRID 433601 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][CH:8]=[C:9](Br)[CH:10]=1)=[O:4].[Li+].[Cl-].[Cl:14][C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][C:20]=1[Cl:21].C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[CH3:1][O:2][C:3](=[O:4])[C:5]1[CH:10]=[C:9]([C:18]2[CH:17]=[CH:16][C:15]([Cl:14])=[C:20]([Cl:21])[CH:19]=2)[CH:8]=[N:7][CH:6]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 433294Lithium ChlorideHCID 699336Methyl 5-bromopyridine-3-carboxylateHCID 27343303,4-Dichlorobenzeneboronic acid

Product 1

HCID 69041910HCID 69041910, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 5-bromopyridine-3-carboxylic acid methyl ester (2 g, 9.3 mmol) in toluene (50 ml) was added tetrakis-(triphenylphosphine)-palladium (0) (320 mg, 0.28 mmol) followed by LiCl (785 mg, 18.5 mmol) and the mixture was stirred 30 min at 20° C. Then 3,4-dichlorophenyl boronic acid (50 wt % in THF/H2O 9:1) (3.7 g, 3.3 ml, 9.7 mmol) and 2N aq. K2CO3 (11.3 ml, 2.5 eq.) were added and the stirred mixture heated under an argon atmosphere at 100° C. for 23 h. After cooling, H2O was added (25 ml) and the aqueous phase separated and extracted with AcOEt. The combined organic extracts were washed with saturated NaCl solution, dried with Na2SO4, filtered and the solvent evaporated and the product dried under high vacuum at 50° C. for 2 h to afford the title compound (2.48g, 95%) as a beige solid. MS: m/e=281.0 (M+H+).

Workup

  1. temperaturethe stirred mixture heated under an argon atmosphere at 100° C. for 23 h
  2. temperatureAfter cooling
  3. customthe aqueous phase separated
  4. extractionextracted with AcOEt
  5. washThe combined organic extracts were washed with saturated NaCl solution
  6. dry with materialdried with Na2SO4
  7. filtrationfiltered
  8. customthe solvent evaporated
  9. customthe product dried under high vacuum at 50° C. for 2 h

Sources & evidence

ORD record
ord-f64772cde8354944a2dd5996dae53647
Source dataset
uspto-grants-2003_12
Patent number
US06667335B2

Reaction notes

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