Boron tribromide → [4-(2-Azepan-1-yl-ethoxy)-phenyl][2-(2,5-difluorophenyl)-6-hydroxynaphthalen-1-yl]-methanone

HRID 1513962Notes

Reaction equation

HRID 1513962 reaction equation
[N:1]1([CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([C:19]3[C:28]4[C:23](=[CH:24][C:25]([O:29]C)=[CH:26][CH:27]=4)[CH:22]=[CH:21][C:20]=3[C:31]3[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:32]=3[F:38])=[O:18])=[CH:13][CH:12]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.B(Br)(Br)Br.C(=O)(O)[O-].[Na+].C(Cl)(Cl)Cl.C(O)(C)C>C(Cl)Cl>[N:1]1([CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([C:19]3[C:28]4[C:23](=[CH:24][C:25]([OH:29])=[CH:26][CH:27]=4)[CH:22]=[CH:21][C:20]=3[C:31]3[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:32]=3[F:38])=[O:18])=[CH:13][CH:12]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 21906603Chloroform isopropyl alcoholHCID 57552524[4-(2-Azepan-1-yl-ethoxy)-phenyl]-[2-(2,5-difluoro-phenyl)-6-methoxy-naphthalen-1-yl]-methanone

Product 1

HCID 67004614[4-(2-Azepan-1-yl-ethoxy)-phenyl][2-(2,5-difluorophenyl)-6-hydroxynaphthalen-1-yl]-methanoneYield 46.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve [4-(2-azepan-1-yl-ethoxy)-phenyl]-[2-(2,5-difluoro-phenyl)-6-methoxy-naphthalen-1-yl]-methanone (1.74 g, 3.37 mmol) in 20 mL methylene chloride and chill in ice. Add to this solution 2.0 mL of boron tribromide (5.3 g, 21.2 mmol) and allow to come to room temperature. Pour into a two phase solution of saturated sodium bicarbonate and 3/1 chloroform/isopropanol. Separate the organic layer, wash with water and dry over 3 Å sieves. Evaporate the solvent and purify on a silica gel column eluting with a 0-10% methanol/methylene chloride gradient. Evaporate the solvent to yield 780 mg (46%) of the title compound.

Workup

  1. temperaturechill in ice
  2. customto come to room temperature
  3. customSeparate the organic layer
  4. washwash with water
  5. customdry over 3 Å sieves
  6. customEvaporate the solvent
  7. custompurify on a silica gel column
  8. washeluting with a 0-10% methanol/methylene chloride gradient
  9. customEvaporate the solvent

Sources & evidence

ORD record
ord-f08f20ce183c4dc3adaef2f5ab105011
Source dataset
uspto-grants-2012_07
Patent number
US08217032B2

Reaction notes

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