Sodium Bicarbonate → HCID 89443836, compound

HRID 1771715Notes

Reaction equation

HRID 1771715 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)[CH:11]=1)[C:6]([OH:8])=O)#[N:2].[NH2:19][C:20]1[C:21]([F:28])=[C:22]([OH:27])[CH:23]=[CH:24][C:25]=1[F:26].C([O-])(O)=O.[Na+]>O=S(Cl)Cl.C1COCC1>[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)[CH:11]=1)[C:6]([NH:19][C:20]1[C:25]([F:26])=[CH:24][CH:23]=[C:22]([OH:27])[C:21]=1[F:28])=[O:8])#[N:2]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 227559833-Amino-2,4-difluorophenolHCID 89443880HCID 89443880, compound

Product 1

HCID 89443836HCID 89443836, compoundYield 67.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 24386Thionyl ChlorideSolvent

Procedure

3-Cyano-5-(3-fluorophenyl)benzoic acid (500 mg, 2.1 mmol, 1 eq) was dissolved in SOCl2 (15 mL) and heated at reflux overnight. The excess SOCl2 was removed under reduced pressure and the residue that remained dissolved in THF (10 mL) and added dropwise to a mixture of 3-amino-2,4-difluorophenol (280 mg, 2 mmol, 0.95 eq) and NaHCO3 (880 mg, 10.5 mmol, 5 eq) in THF (40 mL). The reaction was stirred at room temperature for 3 h, then filtered and the filtrate concentrated in vacuo. The residue was purified by column chromatography (petroleum ether: EtOAc, 10:1) to give the title compound as a white solid (500 mg, 64%).

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. customThe excess SOCl2 was removed under reduced pressure
  4. dissolutionthe residue that remained dissolved in THF (10 mL)
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated in vacuo
  7. customThe residue was purified by column chromatography (petroleum ether: EtOAc, 10:1)

Sources & evidence

ORD record
ord-225847c53064427c885b0b44ca8d4496
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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