Potassium Carbonate → 3-(Pyridin-3-Yl)Benzaldehyde

HRID 1596203Notes

Reaction equation

HRID 1596203 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].C(B(CC)[C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)C.C(=O)([O-])[O-].[K+].[K+]>COCCOC>[N:15]1[CH:16]=[CH:17][CH:18]=[C:13]([C:2]2[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=2)[CH:5]=[O:6])[CH:14]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 765833-BromobenzaldehydeHCID 6428513-(Diethylboryl)pyridine

Product 1

HCID 27955763-(Pyridin-3-Yl)BenzaldehydeYield 73%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

3-Bromobenzaldehyde (5 g, 27 mmol), diethyl (pyridin-3-yl)borane (3.97 g, 27 mmol) and potassium carbonate (11 g, 81 mmol) were dissolved in ethylene glycol dimethyl ether and water (40 ml, 2:1) and degassed under N2 then heated at 80° C. for 18 h after addition of tetrakis(triphenylphosphine)palladium(0) (0.2 g). The reaction was then diluted with ethyl acetate and water (200 ml, 1:1) and passed through a hyflo filter plug, the separated organic phase was washed with brine, dried (MgSO4) and evaporated to dryness. Purified on SiO2 eluting with 25-50% ethyl acetate-hexane to afford the title compound (3.6 g, 73%). MS (ES+) m/e 184 [MH]+.

Workup

  1. customwater (40 ml, 2:1) and degassed under N2
  2. additionafter addition of tetrakis(triphenylphosphine)palladium(0) (0.2 g)
  3. additionThe reaction was then diluted with ethyl acetate and water (200 ml, 1:1)
  4. filtrationfilter plug
  5. washthe separated organic phase was washed with brine
  6. dry with materialdried (MgSO4)
  7. customevaporated to dryness
  8. customPurified on SiO2 eluting with 25-50% ethyl acetate-hexane

Sources & evidence

ORD record
ord-cecd1284dd9141da8070c2914be0d866
Source dataset
uspto-grants-2001_09
Patent number
US06291460B1

Reaction notes

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