Potassium Iodide → 4-(Biphenyl-4-ylaminomethyl)-5-methyl-furan-2-carboxylic acid methyl ester

HRID 1786629Notes

Reaction equation

HRID 1786629 reaction equation
[I-].[K+].[C:3]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.[CH3:16][O:17][C:18]([C:20]1[O:21][C:22]([CH3:27])=[C:23]([CH2:25]Cl)[CH:24]=1)=[O:19].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[CH3:16][O:17][C:18]([C:20]1[O:21][C:22]([CH3:27])=[C:23]([CH2:25][NH:9][C:6]2[CH:5]=[CH:4][C:3]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:8][CH:7]=2)[CH:24]=1)=[O:19]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 71024-AminobiphenylHCID 11430Potassium CarbonateHCID 914782Methyl 4-(chloromethyl)-5-methylfuran-2-carboxylate

Product 1

HCID 588241954-(Biphenyl-4-ylaminomethyl)-5-methyl-furan-2-carboxylic acid methyl esterYield 71.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Potassium iodide (32 mg) and a solution of biphenyl-4-ylamine (74 mg, 0.438 mmoles) in tetrahydrofuran (1 ml) was added to a mixture of 4-chloromethyl-5-methyl-furan-2-carboxylic acid methyl ester (159) (75 mg, 0.398 mmoles) and potassium carbonate (83 mg) in tetrahydrofuran (1 ml). The mixture was stirred at room temperature under an argon atmosphere for 16 hours, and then refluxed with the exclusion of light for 16 hours. After cooling, the mixture was concentrated and the residue was purified by flash chromatography, using a gradient elution of petrol/diethyl ether 9:1 v/v to 4:1 v/v, to afford compound 158 (91 mg). LC/MS System A; Rt=3.93 mins, m/z (ES+)=322 (M+H for C20H19NO3).

Workup

  1. temperaturerefluxed with the exclusion of light for 16 hours
  2. temperatureAfter cooling
  3. concentrationthe mixture was concentrated
  4. customthe residue was purified by flash chromatography
  5. washa gradient elution of petrol/diethyl ether 9:1 v/v to 4:1 v/v

Sources & evidence

ORD record
ord-80ca010d9cf343f0a90c04484c6401ac
Source dataset
uspto-grants-2009_03
Patent number
US07507754B2

Reaction notes

Loading…