1,4-Dioxane → HCID 59205179, compound

HRID 1712076Notes

Reaction equation

HRID 1712076 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[CH:8]=[O:9].P([O-])([O-])([O-])=O.[K+].[K+].[K+].O1[CH2:23][CH2:22][O:21][CH2:20]C1>C(OCC)(=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH:8]([C:3]1[CH:2]=[CH:7][C:22]([O:21][CH3:20])=[C:23]([C:2]2[CH:7]=[CH:6][N:5]=[CH:4][C:3]=2[CH:8]=[O:9])[CH:4]=1)=[O:9]

Participants

6

Reactant 3

HCID 312751,4-DioxaneHCID 62657Potassium Phosphate, TribasicHCID 111167404-Bromopyridine-3-carbaldehyde

Product 1

HCID 59205179HCID 59205179, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A flask was charged with 4-bromo-pyridine-3-carbaldehyde (93 mg, 0.5 mmol), 5-formal-2-methoxylphenelboronic acid (88 mg, 0.6 mmol), tetrakis(triphenylphosphine) palladium(0) (29 mg, 0.025 mmol), potassium phosphate (160 mg, 0.75 mmol) and 1,4-dioxane (5 mL). The reaction mixture was kept at 50° C. overnight. The reaction mixture was then diluted with ethyl acetate and washed with water then brine. The organic layer was dried over sodium sulfate, concentrated, and the residue purified by flash chromatography to yield 4-(5-formyl-2-methoxy-phenyl)-pyridine-3-carbaldehyde as a yellow solid.

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated
  4. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-2e9d5f3fa87b43bf9474dae7514ef185
Source dataset
uspto-grants-2010_09
Patent number
US07790895B2

Reaction notes

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