HCID 89443857, compound → 3-[[2-Chloro-5-(3-fluorophenyl)phenyl]methylamino]-2,4-di fluoro-phenol

HRID 1771647Notes

Reaction equation

HRID 1771647 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=2)=[CH:16][C:3]=1[C:4]([NH:6][C:7]1[C:12]([F:13])=[CH:11][CH:10]=[C:9]([OH:14])[C:8]=1[F:15])=O>C1COCC1>[Cl:1][C:2]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=2)=[CH:16][C:3]=1[CH2:4][NH:6][C:7]1[C:8]([F:15])=[C:9]([OH:14])[CH:10]=[CH:11][C:12]=1[F:13]

Participants

3

Reactant 1

HCID 89443857HCID 89443857, compound

Product 1

HCID 894452343-[[2-Chloro-5-(3-fluorophenyl)phenyl]methylamino]-2,4-di fluoro-phenolYield 103.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of 2-chloro-N-(2,6-difluoro-3-hydroxy-phenyl)-5-(3-fluorophenyl)benzamide (150 mg, 0.34 mmol, 1.0 eq) in THF (3 mL) was added a solution of BH3 (1M in THF, 1.72 mL, 1.72 mmol, 5.0 eq). The reaction was heated at 60° C. for 3 h, then quenched by addition of 1M HCl. The aqueous layer was extracted with EtOAc and the organic extract was washed with water and brine, dried (Na2SO4) filtered and evaporated in vacuo. The residue obtained was purified by flash chromatography (petroleum ether:EtOAc, 100:1 to 30:1) to give the title compound as a colourless oil (128 mg, 89%).

Workup

  1. customquenched by addition of 1M HCl
  2. extractionThe aqueous layer was extracted with EtOAc
  3. extractionthe organic extract
  4. washwas washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe residue obtained
  9. customwas purified by flash chromatography (petroleum ether:EtOAc, 100:1 to 30:1)

Sources & evidence

ORD record
ord-539d49bfb5d74e62b520f0b32dddc8bb
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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