Potassium Carbonate → 4-(5-Chloro-2-hydroxyphenyl)pyridine-2-carbaldehyde

HRID 1692360Notes

Reaction equation

HRID 1692360 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6](B(O)O)[CH:7]=1.Br[C:13]1[CH:18]=[CH:17][N:16]=[C:15]([CH:19]=[O:20])[CH:14]=1.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>C(OCC)(=O)C.O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([CH:19]=[O:20])[CH:14]=2)[CH:7]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 147614724-Bromopyridine-2-carbaldehydeHCID 23005362(5-Chloro-2-hydroxyphenyl)boronic Acid (contains varying amounts of Anhydride)

Product 1

HCID 1360636234-(5-Chloro-2-hydroxyphenyl)pyridine-2-carbaldehydeYield 22.1%

Reagents, catalysts & solvents 3

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

(5-Chloro-2-hydroxyphenyl)boronic acid (1.58 g, 0.00914 mol) was combined with 4-bromopyridine-2-carbaldehyde (1.70 g, 0.0091 mol), bis(triphenylphosphine)palladium (II) chloride (0.321 g, 0.00046 mol) and potassium carbonate (3.16 g, 0.0228 mol) in a 5 mL microwave vial. 1,4-dioxane (3 mL) and water (0.2 mL) were added and heated to 100° C. for 50 minutes in the microwave. The reaction was diluted with ethyl acetate (30 mL) and water (20 mL), filtered, the organic phase was separated then dried over anhydrous sodium sulphate, concentrated in vacuo and purified by flash column chromatography, ISCO™ (80 g column, eluting with 100% heptane to 50% v/v ethyl acetate in heptane) to give the title compound as a beige solid (0.47 g).

Workup

  1. filtrationfiltered
  2. customthe organic phase was separated
  3. dry with materialthen dried over anhydrous sodium sulphate
  4. concentrationconcentrated in vacuo
  5. custompurified by flash column chromatography, ISCO™ (80 g column
  6. washeluting with 100% heptane to 50% v/v ethyl acetate in heptane)

Sources & evidence

ORD record
ord-3d57f4bafc6b4f45a6b59d880e87bcaa
Source dataset
uspto-grants-2012_04
Patent number
US08153814B2

Reaction notes

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