Ethanol → HCID 19093476, compound

HRID 487071Notes

Reaction equation

HRID 487071 reaction equation
[Br:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[C:6]([CH:8]=[O:9])[CH:7]=1.Cl[C:14]1[N:23]=[CH:22][CH:21]=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17].C(O)C.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([C:14]2[N:23]=[CH:22][CH:21]=[CH:20][C:15]=2[C:16]([O:18][CH3:19])=[O:17])[CH:5]=[C:6]([CH:8]=[O:9])[CH:7]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 516892Sodium BicarbonateHCID 819931Methyl 2-chloronicotinateHCID 19093459(3-Bromo-5-formylphenyl)boronic acid

Product 1

HCID 19093476HCID 19093476, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1.14 g (5 mmoles) of 3-bromo-5-formyl-phenylboronic acid, 1.715 g (10 mmoles) of methyl 2-chloro-nicotinate, 100 mg of tetrakis-(triphenyl phosphine)palladium, 2.5 mL of ethanol, 10 mL of 2M sodium bicarbonate solution, and 10 mL of toluene was heated 20 hrs at 80° under nitrogen. After diluting with ethyl acetate, the reaction mixture was washed with saturated NaCl solution. The organic phase was dried over anhydrous MgSO4. Solvent removal gave a crude product which was purified on silica using ethyl acetate:hexane mixture as solvent to give the desired product as a solid.

Workup

  1. temperaturewas heated 20 hrs at 80° under nitrogen
  2. washthe reaction mixture was washed with saturated NaCl solution
  3. dry with materialThe organic phase was dried over anhydrous MgSO4
  4. customSolvent removal
  5. customgave a crude product which
  6. customwas purified on silica

Sources & evidence

ORD record
ord-70fb88c322954721b84298d2d4ca549e
Source dataset
uspto-grants-1994_03
Patent number
US05294610

Reaction notes

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