Triethylamine → 2-(3-((6-Fluoropyridin-3-yl)oxy)phenyl)ethanol

HRID 384126

Reaction equation

HRID 384126 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1.[F:11][C:12]1[N:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[F:11][C:12]1[N:17]=[CH:16][C:15]([O:10][C:6]2[CH:5]=[C:4]([CH2:3][CH2:2][OH:1])[CH:9]=[CH:8][CH:7]=2)=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 834043-Hydroxyphenethyl alcoholHCID 2783397(6-Fluoropyridin-3-yl)boronic acid

Product 1

HCID 684312162-(3-((6-Fluoropyridin-3-yl)oxy)phenyl)ethanol

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6212ChloroformSolvent

Procedure

To a solution of 3-(2-hydroxyethyl)phenol (142.5 mg) in chloroform (5 ml), 279 mg of (6-fluoro-3-pyridinyl)boronic acid, 0.043 ml of triethylamine, 681 mg of copper acetate, and 500 mg of 4A molecular sieve were added, and the reaction solution was stirred at room temperature for 6 days. The reaction solution was filtered through Celite, and the filtrate was diluted with water, extracted with chloroform, and dried over anhydrous magnesium sulfate. The reaction solvent was distilled off under reduced pressure, and the residue obtained was purified by silica gel column chromatography (eluent: ethyl acetate/hexane (0:100-50:50-75/25)) to afford the title compound as a yellow oil.

Workup

  1. filtrationThe reaction solution was filtered through Celite
  2. additionthe filtrate was diluted with water
  3. extractionextracted with chloroform
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe reaction solvent was distilled off under reduced pressure
  6. customthe residue obtained
  7. customwas purified by silica gel column chromatography (eluent: ethyl acetate/hexane (0:100-50:50-75/25))

Sources & evidence

ORD record
ord-3f6bf3bb23f34917aa941651a5ed5c94
Source dataset
uspto-grants-2013_02
Patent number
US08367708B2

Linked notes

Loading…