Water → 4-(Pyridin-4-yl)naphth-1-ylacetic acid

HRID 1936711Notes

Reaction equation

HRID 1936711 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][C:13]([OH:15])=[O:14])=[CH:4][CH:3]=1.[N:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.C(=O)([O-])O.[Na+].O>COCCOC.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>[N:16]1[CH:21]=[CH:20][C:19]([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([CH2:12][C:13]([OH:15])=[O:14])=[CH:4][CH:3]=2)=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 962WaterHCID 215772-(4-Bromonaphthalen-1-yl)acetic acidHCID 516892Sodium BicarbonateHCID 2734379(Pyridin-4-yl)boronic acid

Product 1

HCID 224625334-(Pyridin-4-yl)naphth-1-ylacetic acid

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

4-Bromonaphth-1-ylacetic acid (J. Org. Chem., 1951, 16, 1588) (1 g, 3.78 mmole) in 1,2-dimethoxyethane (50 ml) was treated with pyridin-4-ylboronic acid (465 mg, 3.78 mmole), sodium hydrogen carbonate (952 mg, 11.3 mmole) and water (10 ml). A stream of argon was bubbled through the mixture for 15 minutes, then tetrakis(triphenylphosphine)palladium (0) (200 mg 0.17 mmole) was added and the mixture heated under reflux for 18 hours. The mixture was then concentrated in vacuo to a gum, which was partitioned between 2M sodium hydroxide solution and dichloromethane. The aqueous layer was separated, adjusted to pH 0 with 6M hydrochloric acid and washed with dichloromethane; then adjusted to pH 7 by addition of aqueous potassium carbonate solution and extracted with dichloromethane. The dichloromethane extract was dried (Na2SO4) and concentrated in vacuo to give the title compound, which crystallised from ether as needles mp 210-215° C. (465 mg, 46%).

Workup

  1. customA stream of argon was bubbled through the mixture for 15 minutes
  2. temperaturethe mixture heated
  3. temperatureunder reflux for 18 hours
  4. concentrationThe mixture was then concentrated in vacuo to a gum, which
  5. customwas partitioned between 2M sodium hydroxide solution and dichloromethane
  6. customThe aqueous layer was separated
  7. washwashed with dichloromethane
  8. additionthen adjusted to pH 7 by addition of aqueous potassium carbonate solution
  9. extractionextracted with dichloromethane
  10. extractionThe dichloromethane extract
  11. dry with materialwas dried (Na2SO4)
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-59519289fdff46fab81229f1a948fb53
Source dataset
uspto-grants-2002_05
Patent number
US06391891B1

Reaction notes

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