2-Fluoro-5-(3-fluorophenyl)-N-(3-methoxyphenyl)benzamide → N-[[2-Fluoro-5-(3-fluorophenyl)phenyl]methyl]-3-methoxy-aniline

HRID 1771588Notes

Reaction equation

HRID 1771588 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=2)=[CH:15][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[CH:8]=1)=O>C1COCC1>[F:1][C:2]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=2)=[CH:15][C:3]=1[CH2:4][NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[CH:8]=1

Participants

3

Reactant 1

HCID 894442352-Fluoro-5-(3-fluorophenyl)-N-(3-methoxyphenyl)benzamide

Product 1

HCID 89443597N-[[2-Fluoro-5-(3-fluorophenyl)phenyl]methyl]-3-methoxy-anilineYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-fluoro-5-(3-fluorophenyl)-N-(3-methoxyphenyl)benzamide (605 mg, 1.80 mmol, 1.0 eq) in THF (3 mL) was added dropwise a solution of BH3 (1 M in THF, 5.3 mL, 5.3 mmol, 2.9 eq) at 0° C. The reaction was heated at reflux overnight, then cooled to room temperature and quenched by addition of methanol and water. The reaction was diluted with EtOAc and water and the aqueous layer extracted further with EtOAc. The combined organic extracts were washed with brine, dried (Na2SO4), filtered and evaporated in vacuo. The crude residue was purified by flash chromatography (petroleum ether: EtOAc, 10:1) to give the title compound as a colourless oil (512 mg, 88%).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux overnight
  3. customquenched by addition of methanol and water
  4. additionThe reaction was diluted with EtOAc and water
  5. extractionthe aqueous layer extracted further with EtOAc
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customThe crude residue was purified by flash chromatography (petroleum ether: EtOAc, 10:1)

Sources & evidence

ORD record
ord-5738ab863104419eaf325a03d1128bc3
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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