Water → 3-Methyl-4-pyridinecarboxaldehyde

HRID 2092045Notes

Reaction equation

HRID 2092045 reaction equation
Cl[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH:8]=[O:9].[CH3:10]B1OB(C)OB(C)O1.C(=O)([O-])[O-].[K+].[K+].O>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O1CCOCC1>[CH3:10][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH:8]=[O:9]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 27629953-Chloro-4-pyridinecarboxaldehyde

Product 1

HCID 15018803-Methyl-4-pyridinecarboxaldehyde

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

3-Chloropyridine-4-carbaldehyde (141.6 mg, 1.00 mmol), trimethylboroxine (278.4 μl 2.00 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) dichloromethane complex (81.6 mg, 0.10 mmol) and potassium carbonate (414.6 mg, 3.00 mmol) were mixed with water (0.2 mL) and 1,4-dioxane (1.8 mL) and stirred at 100° C. for 3 hours. After completion of the reaction, the reaction solution was allowed to cool, and the solvent was removed by vacuum distillation. The resulting crude reaction product containing the desired product was used for the next step (594.7 mg).

Workup

  1. customAfter completion of the reaction
  2. temperatureto cool
  3. customthe solvent was removed by vacuum distillation
  4. customThe resulting crude reaction product

Sources & evidence

ORD record
ord-9e91555c9a4440c6a1795341aa1d5a84
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

Loading…