Phenylboronic Acid → 2-phenyl-quinoline-3-carbaldehyde

HRID 2187644Notes

Reaction equation

HRID 2187644 reaction equation
Cl[C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[C:14]1(B(O)O)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:14]1([C:2]2[C:11]([CH:12]=[O:13])=[CH:10][C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 2

HCID 66827Phenylboronic AcidHCID 6909582-Chloro-3-quinolinecarboxaldehyde

Product 1

HCID 121916842-phenyl-quinoline-3-carbaldehydeYield 90%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 10340Sodium CarbonateSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 960 mg (5 mmol) of 2-chloroquinolin-3-carbaldehyde, 570 mg (0.5 mmol) of Pd(PPh3)4, and 1.2 g of benzeneboronic acid in a mixture of 7.5 ml of 2M aqueous sodium carbonate solution and 20 ml of dioxane was heated for 40 h to 95° C. It was extracted with ethyl acetate, and the organic layer was dried and evaporated. The residue was chromatographed on silica gel with a hexane/ethyl acetate gradient 98:2 to 90:10 to give 1.05 g (90%) of the title aldehyde.

Workup

  1. temperaturewas heated for 40 h to 95° C
  2. extractionIt was extracted with ethyl acetate
  3. customthe organic layer was dried
  4. customevaporated
  5. customThe residue was chromatographed on silica gel with a hexane/ethyl acetate gradient 98:2 to 90:10

Sources & evidence

ORD record
ord-aaebedc04a634dfa837938e5b8c6eafe
Source dataset
uspto-grants-2002_06
Patent number
US06410562B1

Reaction notes

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