Pyridine → HCID 58542000, compound

HRID 1966701Notes

Reaction equation

HRID 1966701 reaction equation
[CH:1]([C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1B(O)O)=[O:2].[CH3:14][C:15]1[CH:19]=[CH:18][NH:17][N:16]=1.N1C=CC=CC=1>C(Cl)Cl.CN(C=O)C.CC([O-])=O.CC([O-])=O.[Cu+2]>[CH3:10][O:9][C:7]1[CH:6]=[CH:5][C:4]([N:17]2[CH:18]=[CH:19][C:15]([CH3:14])=[N:16]2)=[C:3]([CH:8]=1)[CH:1]=[O:2]

Participants

7

Reactant 3

HCID 1049PyridineHCID 27343652-Formyl-4-methoxybenzeneboronic acidHCID 178428694HCID 178428694, compound

Product 1

HCID 58542000HCID 58542000, compoundYield 4.3%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-formyl-4-methoxyphenylboronic acid (2.5 g, 13.89 mmol) in CH2Cl2 (30 mL) and DMF (15 mL) are added 3-methyl-1H-pyrazole (0.80 g, 9.72 mmol), Cu(OAc)2 (3.78 g, 20.84 mmol), pyridine (2.27 mL, 27.78 mmol) and molecular sieves (2.5 g) at room temperature. The mixture is stirred at the same temperature for 5 days with loose cap. The mixture is filtered through a short pad of diatomaceous earth and the solids are washed with CH2Cl2. The combined filtrates are concentrated and the remaining residue is diluted with water and ethyl acetate. The layers are separated and the aqueous phase extracted with EtOAc (3×). The combined organics are dried (MgSO4), filtered, and concentrated. The remaining residue is purified via flash chromatography (silica gel, 0-15% EtOAc/heptane) to afford 5-methoxy-2-(3-methyl-pyrazol-1-yl)-benzaldehyde (90 mg, 3%).

Workup

  1. filtrationThe mixture is filtered through a short pad of diatomaceous earth
  2. washthe solids are washed with CH2Cl2
  3. concentrationThe combined filtrates are concentrated
  4. additionthe remaining residue is diluted with water and ethyl acetate
  5. customThe layers are separated
  6. extractionthe aqueous phase extracted with EtOAc (3×)
  7. dry with materialThe combined organics are dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe remaining residue is purified via flash chromatography (silica gel, 0-15% EtOAc/heptane)

Sources & evidence

ORD record
ord-1b5f7c6946354f8fae14ef186e2ca58b
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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