Ethyl Acetate → HCID 18473985, compound

HRID 564843Notes

Reaction equation

HRID 564843 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:11][CH2:12]NC(C)C)=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[CH3:17][N:18]([CH3:35])[C:19]1[O:20][CH:21]([C:25]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:26])[C:22](=[O:24])[N:23]=1.C(P(CCCC)CCCC)CCC.C(OCC)(=O)C>C(#N)C.C(OCC)C>[CH3:17][N:18]([CH3:35])[C:19]1[O:20][C:21]([CH:11]([C:6]2[C:5]3[C:9](=[CH:10][C:2]([F:1])=[CH:3][CH:4]=3)[NH:8][CH:7]=2)[CH3:12])([C:25]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:26])[C:22](=[O:24])[N:23]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 13831TributylphosphineHCID 11821403HCID 11821403, compoundHCID 70158934HCID 70158934, compound

Product 1

HCID 18473985HCID 18473985, compoundYield 60.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

To a mixture of 6-fluoro-3-(1-isopropylamino)ethylindole (435 mg), benzyl 2-dimethylamino-4-oxo-2-oxazolin-5-carboxylate (518 mg) in acetonitrile (15 ml) was added tri-n-butylphosphine (492 μl). The mixture was refluxed for 2.5 hours. Removal of the solvent gave a residue, to which a mixture of ethyl acetate and ethyl ether in a ration of 10:1 was added to provide benzyl 2-dimethylamino-5-[1-(6-fluoroindol-3-yl)ethyl]-4-oxo-2-oxazolin-5-carboxylate (509 mg) as a crystal.

Workup

  1. temperatureThe mixture was refluxed for 2.5 hours
  2. customRemoval of the solvent
  3. customgave a residue
  4. additionwas added

Sources & evidence

ORD record
ord-c0f64f2d27ca4e0bb07f6c3533cf9b55
Source dataset
uspto-grants-2001_01
Patent number
US06169102A

Reaction notes

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