Acetonitrile → [2-(2,5-Difluorophenyl)-6-hydroxynaphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone

HRID 1513955Notes

Reaction equation

HRID 1513955 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:19]C)[CH:15]=2)[C:10]=1[C:21]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][N:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)=[CH:25][CH:24]=1)=[O:22].B(Br)(Br)Br.C(#N)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:19])[CH:15]=2)[C:10]=1[C:21]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][N:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)=[CH:25][CH:24]=1)=[O:22]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 57552548[2-(2,5-Difluoro-phenyl)-6-methoxy-naphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone

Product 1

HCID 67004531[2-(2,5-Difluorophenyl)-6-hydroxynaphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanoneYield 87.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Convert [2-(2,5-difluoro-phenyl)-6-methoxy-naphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone (1.8 g, 3.5 mmol) to the hydrochloride salt and dissolve it in 300 mL methylene chloride. Chill the mixture in ice and slowly add boron tribromide (5.0 mL, 53.0 mmol) with swirling. Allow the mixture to come to room temperature and stir for two hours. Add to this mixture acetonitrile (15 mL) slowly and with stirring which produces an orange precipitate. Pour the mixture into saturated sodium bicarbonate with stirring, separate the organic layer and dry with molecular sieves to give 1.5 g of the title compound (86%).

Workup

  1. temperatureChill the mixture in ice
  2. customto come to room temperature
  3. stirringwith stirring which
  4. customproduces an orange precipitate
  5. stirringwith stirring
  6. customseparate the organic layer
  7. customdry with molecular sieves

Sources & evidence

ORD record
ord-60d81fabc8e84d749c6ba13d52f7e4d8
Source dataset
uspto-grants-2012_07
Patent number
US08217032B2

Reaction notes

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