Iodoethane → 5-(Ethyl-isobutyryl-amino)-4'-methyl-biphenyl-3-carboxylic acid methyl ester

HRID 340622Notes

Reaction equation

HRID 340622 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)[CH:8]=[C:9]([NH:11][C:12](=[O:16])[CH:13]([CH3:15])[CH3:14])[CH:10]=1)=[O:4].[H-].[Na+].[CH2:26](I)[CH3:27]>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)[CH:8]=[C:9]([N:11]([CH2:26][CH3:27])[C:12](=[O:16])[CH:13]([CH3:15])[CH3:14])[CH:10]=1)=[O:4]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 596275325-Isobutyrylamino-4'-methyl-biphenyl-3-carboxylic acid methyl ester

Product 1

HCID 596275275-(Ethyl-isobutyryl-amino)-4'-methyl-biphenyl-3-carboxylic acid methyl esterYield 58.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Isobutyrylamino-4′-methyl-biphenyl-3-carboxylic acid methyl ester (0.786 g, 2.32 mmol) and NaH (6.2 g, 2.55 mmol) were added to DMF (20 mL), and the mixture was stirred for 30 minutes at room temperature, then cooled to 0° C. Ethyl iodide (1.181 g, 11.6 mmol) was added, and the reaction mixture was stirred for five days at room temperature. The reaction was quenched by addition of saturated aqueous NH4Cl and water, and the mixture was extracted with diethyl ether. The combined organic layers were separated, washed with water and brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (30% ethyl acetate in hexanes) to give 0.461 g of 5-(ethyl-isobutyryl-amino)-4′-methyl-biphenyl-3-carboxylic acid methyl ester.

Workup

  1. temperaturecooled to 0° C
  2. stirringthe reaction mixture was stirred for five days at room temperature
  3. customThe reaction was quenched by addition of saturated aqueous NH4Cl and water
  4. extractionthe mixture was extracted with diethyl ether
  5. customThe combined organic layers were separated
  6. washwashed with water and brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by flash chromatography (30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-3a87b63416ae4f43b5f6c87115d1825c
Source dataset
uspto-grants-2014_11
Patent number
US08895589B2

Reaction notes

Loading…