Methanol → 6-(3,5-Difluoro-phenyl)-5-[4-(2-piperidin-1-yl-ethoxy)-phenoxy]-naphthalen-2-ol

HRID 732780Notes

Reaction equation

HRID 732780 reaction equation
Cl.[F:2][C:3]1[CH:4]=[C:5]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:20]C)[CH:16]=3)[C:11]=2[O:22][C:23]2[CH:37]=[CH:36][C:26]([O:27][CH2:28][CH2:29][N:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)=[CH:25][CH:24]=2)[CH:6]=[C:7]([F:9])[CH:8]=1.B(Br)(Br)Br.CO>ClCCl>[F:9][C:7]1[CH:6]=[C:5]([C:10]2[C:11]([O:22][C:23]3[CH:24]=[CH:25][C:26]([O:27][CH2:28][CH2:29][N:30]4[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]4)=[CH:36][CH:37]=3)=[C:12]3[C:17](=[CH:18][CH:19]=2)[CH:16]=[C:15]([OH:20])[CH:14]=[CH:13]3)[CH:4]=[C:3]([F:2])[CH:8]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 685171011-(2-{4-[2-(3,5-Difluoro-phenyl)-6-methoxy-naphthalen-1-yloxy]-phenoxy}-ethyl)-piperidine hydrochloride

Product 1

HCID 670045356-(3,5-Difluoro-phenyl)-5-[4-(2-piperidin-1-yl-ethoxy)-phenoxy]-naphthalen-2-olYield 96.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dissolve 1-(2-{4-[2-(3,5-difluoro-phenyl)-6-methoxy-naphthalen-1-yloxy]-phenoxy}-ethyl)-piperidine hydrochloride (410 mg, 0.76 mmol) in dichloromethane (10 mL) and cool in an ice bath. Add boron tribromide (0.22 mL, 2.28 mmol) and stir for 2.5 hours. Add methanol (5 mL), warm to ambient temperature, dilute with dichloromethane and wash with saturated aqueous sodium bicarbonate, dry with solid magnesium sulfate, filter and remove solvent under vacuum. Chromatograph on silica gel with dichloromethane/methanol mixtures to give 350 mg of the title compound (96%).

Workup

  1. temperaturecool in an ice bath
  2. washwash with saturated aqueous sodium bicarbonate
  3. dry with materialdry with solid magnesium sulfate
  4. filtrationfilter
  5. customremove solvent under vacuum

Sources & evidence

ORD record
ord-8971d52ebfba412a9477aab78c40f7e5
Source dataset
uspto-grants-2009_09
Patent number
US07585977B2

Reaction notes

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