N-(2,6-Difluoro-3-hydroxy-phenyl)-3-(3-fluorophenyl)benzamide → 2,4-Difluoro-3-[[3-(3-fluorophenyl)phenyl]methylamino]phenol

HRID 1771607Notes

Reaction equation

HRID 1771607 reaction equation
[F:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([F:9])[C:3]=1[NH:10][C:11](=O)[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=2)[CH:13]=1>C1COCC1>[F:1][C:2]1[C:3]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=3)[CH:13]=2)=[C:4]([F:9])[CH:5]=[CH:6][C:7]=1[OH:8]

Participants

3

Reactant 1

HCID 89443548N-(2,6-Difluoro-3-hydroxy-phenyl)-3-(3-fluorophenyl)benzamide

Product 1

HCID 894442752,4-Difluoro-3-[[3-(3-fluorophenyl)phenyl]methylamino]phenolYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of N-(2,6-difluoro-3-hydroxy-phenyl)-3-(3-fluorophenyl)benzamide (310 mg, 0.9 mmol, 1.0 eq) in THF (5 mL) was added BH3 (5.4 mL, 1M in THF, 5.4 mmol, 6.0 eq) and the reaction heated at 60° C. overnight. The reaction mixture was quenched with water and extracted with EtOAc. The organic extract was washed with water and brine, dried (Na2SO4) and evaporated in vacuo. The residue was purified by column chromatography (petroleum ether:EtOAc 1:0 to 10:1) to give the title compound as an oil (255 mg, 86%).

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with EtOAc
  3. extractionThe organic extract
  4. washwas washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography (petroleum ether:EtOAc 1:0 to 10:1)

Sources & evidence

ORD record
ord-ac1196616a1e4c9ba367166cfd7a3fa3
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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