Water → HCID 178522204, compound

HRID 526072Notes

Reaction equation

HRID 526072 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([OH:12])[CH:6]=[C:5]2[C:13]([NH:15][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)=[O:14].C(=O)([O-])[O-].[K+].[K+].O.[C:29]1(B(O)O)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CN(C=O)C.C(OCC)(=O)C>[OH:12][C:7]1[CH:6]=[C:5]([C:13]([NH:15][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)=[O:14])[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:3]=2)[N:8]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 1785222036-bromo-2-hydroxy-N-(pyridin-3-yl)quinoline-4-carboxamide

Product 1

HCID 178522204HCID 178522204, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a round-bottomed flask under argon atmosphere was added 6-bromo-2-hydroxy-N-(pyridin-3-yl)quinoline-4-carboxamide (3.00 g) in DMF (50 ml), and the vessel was purged with argon under stirring for 5 minutes. After 5 minutes, 2N solution of potassium carbonate in water (11 eq) was added and the flask was purged with argon under stirring for 5 minutes. Phenylboronic acid (1.5 eq) was then added and the tube was purged with argon under stirring for 15 minutes. Finally, palladium(0)tetrakis triphenylphosphine (0.03 eq) was added under argon and the flask was affixed to a reflux condenser and heated to 80° C. for 5 hours. The completion of the reaction was monitored on TLC using ethyl acetate:hexanes (5:5) as a mobile phase. After completion of the reaction, reaction mixture was diluted with ethyl acetate (100 ml) and then washed with water (5*100 ml). The ethyl acetate layer was dried over anhydrous sodium sulphate and then solvent was distilled out and the crude was subjected to purification by silica gel column chromatography to provide 9.0 g of 2-hydroxy-6-phenyl-N-(pyridin-3-yl)quinoline-4-carboxamide.

Workup

  1. customthe vessel was purged with argon
  2. waitAfter 5 minutes
  3. customthe flask was purged with argon
  4. stirringunder stirring for 5 minutes
  5. customthe tube was purged with argon
  6. stirringunder stirring for 15 minutes
  7. customthe flask was affixed to a reflux condenser
  8. customAfter completion of the reaction, reaction mixture
  9. washwashed with water (5*100 ml)
  10. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulphate
  11. distillationsolvent was distilled out
  12. customthe crude was subjected to purification by silica gel column chromatography

Sources & evidence

ORD record
ord-9eaeca1491ce40eca1215b3ba9d6137b
Source dataset
uspto-grants-2016_05
Patent number
US09345700B2

Reaction notes

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