Methyl 5-(3-fluorophenyl)furan-2-carboxylate → HCID 178513053, compound

HRID 898814Notes

Reaction equation

HRID 898814 reaction equation
C[O:2][C:3]([C:5]1[O:6][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=2)=[CH:8][CH:9]=1)=O.CS(O)(=O)=O.FC1C=CC=CC=1C1OC(C([NH:36][C:37]([NH2:39])=[NH:38])=O)=CC=1>CN(C=O)C.[Cl-].[Na+].O>[F:16][C:12]1[CH:11]=[C:10]([C:7]2[O:6][C:5]([C:3]([NH:38][C:37]([NH2:39])=[NH:36])=[O:2])=[CH:9][CH:8]=2)[CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 11229733Methyl 5-(3-fluorophenyl)furan-2-carboxylateHCID 178505355HCID 178505355, compound

Product 1

HCID 178513053HCID 178513053, compoundYield 89.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

5-(3-fluorophenyl)furan-2-carboxylic acid methyl ester (250 mg, 1.14 mmol) was dissolved in DMF (3 ml), to which 2 M guanidine solution (3.4 ml, 6.8 mmol) prepared in Example 1 was added, followed by stirring at room temperature for 2 hours. After completion of the reaction, the solution was added with saturated brine (20 ml) and extracted with ethyl acetate (30 ml×3). The organic layer was washed with 10% brine, dried over anhydrous magnesium sulfate (MgSO4), and concentrated in vacuo. The residue was purified by silica gel column chromatography (5% methanol/dichloromethane), to give 252 mg of a title compound (yield: 89%).

Workup

  1. additionwas added
  2. customAfter completion of the reaction
  3. extractionextracted with ethyl acetate (30 ml×3)
  4. washThe organic layer was washed with 10% brine
  5. dry with materialdried over anhydrous magnesium sulfate (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography (5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-559cc5bd97c24cdaa20cddda31b2d990
Source dataset
uspto-grants-2008_04
Patent number
US07351843B2

Reaction notes

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