Ethyl Acetate → Ethyl 3-(4-[(3-chloro-4-fluorophenyl)amino]carbonyl-1,2,5-oxadiazol-3-yl)propanoate

HRID 1845786Notes

Reaction equation

HRID 1845786 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:12]2[C:13](/[CH:17]=[CH:18]/[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[N:14][O:15][N:16]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[F:8].C(OCC)(=O)C>[Pd]>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:12]2[C:13]([CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[N:14][O:15][N:16]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 58941780Ethyl (2E)-3-(4-[(3-chloro-4-fluorophenyl)amino]carbonyl-1,2,5-oxadiazol-3-yl)acrylate

Product 1

HCID 58941764Ethyl 3-(4-[(3-chloro-4-fluorophenyl)amino]carbonyl-1,2,5-oxadiazol-3-yl)propanoateYield 71.3%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of ethyl (2E)-3-(4-[(3-chloro-4-fluorophenyl)amino]carbonyl-1,2,5-oxadiazol-3-yl)acrylate (0.86 g, 0.0025 mol) in ethyl acetate (10 mL, 0.1 mol) was added palladium (600 mg, 0.006 mol). The mixture was stirred at room temperature under an atmosphere of hydrogen for 2 h. The reaction solution was filtered through a pad of celite. The filtrate was concentrated and purified by flash chromatography (40% ethyl acetate/hexane) to give the desired product as a white solid (609 mg, 70%). LCMS for C14H14ClFN3O4(M+H)+: m/z-=342.1.

Workup

  1. filtrationThe reaction solution was filtered through a pad of celite
  2. concentrationThe filtrate was concentrated
  3. custompurified by flash chromatography (40% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-3a1de1487933470c9ad457305ca0bf85
Source dataset
uspto-grants-2015_02
Patent number
US08951536B2

Reaction notes

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