Water → 6-(4-tert-Butylphenyl)pyridin-3-ol

HRID 660978Notes

Reaction equation

HRID 660978 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[C:9]([C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1)([CH3:12])([CH3:11])[CH3:10].[F-].[K+].O>C1(C)C=CC=CC=1>[C:9]([C:13]1[CH:18]=[CH:17][C:16]([C:2]2[N:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=2)=[CH:15][CH:14]=1)([CH3:12])([CH3:11])[CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 522689Potassium FluorideHCID 8198212-Chloro-5-hydroxypyridineHCID 27343204-tert-Butylphenylboronic acid

Product 1

HCID 532294336-(4-tert-Butylphenyl)pyridin-3-olYield 37.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 6-Chloro-pyridin-3-ol (3.10 g, 23.9 mmol) in toluene (30 ml) is added 4-tert-butyl-phenylboronic acid (5.46 g, 30.6 mmol), potassium fluoride (2.82 g, 47.9 mmol), and palladium tetrakis triphenylphosphine (1.20 g, 1.20 mmol). Water (15 mL) is added and the reaction mixture is heated to reflux overnight. After cooling to rt, the reaction mixture is partitioned between ethyl acetate and water. The aqueous layer is back-extracted with ethyl acetate, the combined organic layers are dried and concentrated. The resulting residue is applied to silica gel and eluted using hexanes with an ethyl acetate gradient to give the title compound (2.06 g).

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureto reflux overnight
  3. customthe reaction mixture is partitioned between ethyl acetate and water
  4. extractionThe aqueous layer is back-extracted with ethyl acetate
  5. customthe combined organic layers are dried
  6. concentrationconcentrated
  7. washeluted

Sources & evidence

ORD record
ord-e97e9f3583d249c9b13a20442345978f
Source dataset
uspto-grants-2011_12
Patent number
US08084489B2

Reaction notes

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