HCID 89443836, compound → HCID 89443808, compound

HRID 1771716Notes

Reaction equation

HRID 1771716 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:18]=[C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=2)[CH:20]=1)[C:6]([NH:8][C:9]1[C:14]([F:15])=[CH:13][CH:12]=[C:11]([OH:16])[C:10]=1[F:17])=O)#[N:2]>C1COCC1>[F:17][C:10]1[C:11]([OH:16])=[CH:12][CH:13]=[C:14]([F:15])[C:9]=1[NH:8][CH2:6][C:5]1[CH:4]=[C:3]([CH:20]=[C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=2)[CH:18]=1)[C:1]#[N:2]

Participants

3

Reactant 1

HCID 89443836HCID 89443836, compound

Product 1

HCID 89443808HCID 89443808, compoundYield 29,267.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

To a solution of 3-Cyano-N-(2,6-difluoro-3-hydroxy-phenyl)-5-(3-fluorophenyl)benzamide (500 mg, 2.7 mmol, 1.0 eq) in THF (30 mL) at 0° C. was added a solution of BH3 (1M in THF, 10.8 mL, 10.8 mmol, 4.0 eq) dropwise. The reaction was then heated at 50° C. for 6 h. The reaction was cooled to room temperature and quenched by addition of aqueous NH4Cl. The aqueous layer was extracted with EtOAc and the combined organic extracts dried (Na2SO4), filtered and evaporated in vacuo. The residue obtained was purified by column chromatography (petroleum ether:EtOAc, 7:1) to give the title compound as white solid (280 g, 58%).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customquenched by addition of aqueous NH4Cl
  3. extractionThe aqueous layer was extracted with EtOAc
  4. dry with materialthe combined organic extracts dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue obtained
  8. customwas purified by column chromatography (petroleum ether:EtOAc, 7:1)

Sources & evidence

ORD record
ord-053f1ee0463045d29516fbcc35fca811
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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