Tetrahydrofuran → (E)-N-(3-Cyano-6-fluoro-5-hydroxy-2-methyl[1,1'-biphenyl]-4-yl)-3-phenyl-2-propenamide

HRID 17349

Reaction equation

HRID 17349 reaction equation
[C:1](Cl)(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O1CCCC1.[NH2:17][C:18]1[C:25]([OH:26])=[C:24]([F:27])[C:23]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[C:22]([CH3:34])[C:19]=1[C:20]#[N:21].C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[C:20]([C:19]1[C:22]([CH3:34])=[C:23]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:24]([F:27])=[C:25]([OH:26])[C:18]=1[NH:17][C:1](=[O:10])/[CH:2]=[CH:3]/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)#[N:21]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 660233-Phenylprop-2-enoyl chlorideHCID 516892Sodium BicarbonateHCID 860974464-Amino-3-cyano-6-fluoro-5-hydroxy-2-methylbiphenyl

Product 1

HCID 86630839(E)-N-(3-Cyano-6-fluoro-5-hydroxy-2-methyl[1,1'-biphenyl]-4-yl)-3-phenyl-2-propenamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Under nitrogen atmosphere, cinnamoyl chloride (378 mg, 2.27 mmol) was dropwise added to a tetrahydrofuran solution (10 ml) of 2-amino-5-phenyl-4-fluoro-3-hydroxy-6-methylbenzonitrile (I-41) (500 mg, 2.06 mmol) and sodium hydrogencarbonate (399 mg, 4.75 mmol) cooled with ice, followed by stirring at room temperature for 17 hours and stirring at 60° C. for 1 hour. After cooling, ethyl acetate was added to the reaction liquid, followed by washing with water and saturated brine. The obtained organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated away under reduced pressure.

Workup

  1. temperaturecooled with ice
  2. stirringstirring at 60° C. for 1 hour
  3. temperatureAfter cooling
  4. washby washing with water and saturated brine
  5. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated away under reduced pressure

Sources & evidence

ORD record
ord-b6f53dcdba73465fa9aca3432bd28b74
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Linked notes

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