Boron tribromide → 3-(4-Hydroxyphenyl)-7-[2-hydroxy-3-({[3-(trifluoromethyl)phenyl]methyl}amino)propoxy]chromen-4-one

HRID 1694661Notes

Reaction equation

HRID 1694661 reaction equation
[OH:1][CH:2]([CH2:24][NH:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=1)[CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9](=[O:23])[C:10]([C:15]3[CH:20]=[CH:19][C:18]([O:21]C)=[CH:17][CH:16]=3)=[CH:11][O:12]2)=[CH:7][CH:6]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:21][C:18]1[CH:17]=[CH:16][C:15]([C:10]2[C:9](=[O:23])[C:8]3[C:13](=[CH:14][C:5]([O:4][CH2:3][CH:2]([OH:1])[CH2:24][NH:25][CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:34])[F:35])[CH:28]=4)=[CH:6][CH:7]=3)[O:12][CH:11]=2)=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 672791297-[2-Hydroxy-3-({[3-(trifluoromethyl)phenyl]methyl}amino)propoxy]-3-(4-methoxyphenyl)chromen-4-one

Product 1

HCID 596606433-(4-Hydroxyphenyl)-7-[2-hydroxy-3-({[3-(trifluoromethyl)phenyl]methyl}amino)propoxy]chromen-4-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of 7-[2-hydroxy-3-({[3-(trifluoromethyl)phenyl]methyl}-amino)propoxy]-3-(4-methoxyphenyl)chromen-4-one (38 mg, 0.076 mmol) in methylene chloride at ° C. was added boron tribromide (1M, 0.38 ml). The resulting mixture was stirred at room temperature for 4 hours, then the solvent removed under reduced pressure. The residue was purified by preparative thin layer chromatography, eluting with 10% methanol/dichloromethane, to provide 3-(4-hydroxyphenyl)-7-[2-hydroxy-3-({[3-(trifluoromethyl)phenyl]methyl}amino)propoxy]chromen-4-one.

Workup

  1. customthe solvent removed under reduced pressure
  2. customThe residue was purified by preparative thin layer chromatography
  3. washeluting with 10% methanol/dichloromethane

Sources & evidence

ORD record
ord-00122799af614046b083d7bb63b3cc65
Source dataset
uspto-grants-2012_04
Patent number
US08158810B2

Reaction notes

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