HCID 89445479, compound → HCID 89445181, compound

HRID 1771689Notes

Reaction equation

HRID 1771689 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[C:17]([F:18])=[CH:16][CH:15]=[C:14]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=2)[C:13]=1[F:26]>C1COCC1>[F:26][C:13]1[C:14]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=2)=[CH:15][CH:16]=[C:17]([F:18])[C:12]=1[CH2:11][NH:10][C:3]1[C:2]([F:1])=[C:7]([OH:8])[CH:6]=[CH:5][C:4]=1[F:9]

Participants

3

Reactant 1

HCID 89445479HCID 89445479, compound

Product 1

HCID 89445181HCID 89445181, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of N-(2,6-difluoro-3-hydroxy-phenyl)-2,6-difluoro-3-(3-fluorophenyl)benzamide (500 mg, 1.32 mmol, 1.0 eq) in THF (10 mL) under N2 was added dropwise a solution of BH3 (1M in THF, 7 mL, 7.0 mmol, 5.3 eq) at room temperature. The reaction mixture was heated at reflux for 4 h then cooled and the reaction was 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 to give the title compound (400 mg, 83%) as an oil which was used in the next step without purification.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 4 h
  3. temperaturethen cooled
  4. customthe reaction was quenched by addition of 1M HCl
  5. extractionThe aqueous layer was extracted with EtOAc
  6. extractionthe organic extract
  7. washwas washed with water and brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-2e42faebff3d4d179c428987b8abd020
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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