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

HRID 1402065Notes

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

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

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

Sources & evidence

ORD record: ord-9bb8b8243eea45ada94f31e56c692a6d
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08907101B2

Reaction notes

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