Sodium ethoxide → 5-Fluoro-6-methyl-1,1'-biphenyl-3-carboxamide

HRID 31469Notes

Reaction equation

HRID 31469 reaction equation
[O-]CC.[Na+].ClCC1OC([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:23]([CH3:24])=[C:22]([F:25])[CH:21]=[C:20]([C:26]([NH:28]C4CC4)=[O:27])[CH:19]=3)=[CH:14][CH:13]=2)=NN=1>C(O)C>[F:25][C:22]1[CH:21]=[C:20]([C:26]([NH2:28])=[O:27])[CH:19]=[C:18]([C:15]2[CH:16]=[CH:17][CH:12]=[CH:13][CH:14]=2)[C:23]=1[CH3:24]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 693149174'-[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-5-fluoro-6-methyl-1,1'-biphenyl-3-carboxamide2×

Product 1

HCID 866046975-Fluoro-6-methyl-1,1'-biphenyl-3-carboxamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Freshly prepared sodium ethoxide in ethanol (0.2M, 0.8 ml) was added to a solution of (4′-[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-5-fluoro-6-methyl-1,1′-biphenyl-3-carboxamide (Intermediate 34) (50 mg) in ethanol (1 ml) and the reaction stirred at room temperature for 18 hours. The reaction was reduced to dryness under vacuum and the residue partitioned between ethyl acetate and water. The organic phase dried (magnesium sulphate) and reduced to dryness under vacuum. The residue was purified by HPLC to give N-cyclopropyl-4′-[5-ethoxymethyl)-1,3,4-oxadiazol-2-yl]-5-fluoro-6-methyl-1,1′-biphenyl-3-carboxamide.

Workup

  1. customthe residue partitioned between ethyl acetate and water
  2. dry with materialThe organic phase dried (magnesium sulphate)
  3. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-01140e8d3fa24085a648bb18a36c93a3
Source dataset
uspto-grants-2008_09
Patent number
US07425555B2

Reaction notes

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