1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 68452356, compound

HRID 2355070Notes

Reaction equation

HRID 2355070 reaction equation
Br[C:2]1[O:6][C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[N:4][N:3]=1.[Br:12][C:13]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:14]=1[O:15][C@H:16]1[CH2:20][CH2:19][NH:18][CH2:17]1.C1CCN2C(=NCCC2)CC1>C1COCC1>[CH2:10]([O:9][C:7]([C:5]1[O:6][C:2]([N:18]2[CH2:19][CH2:20][C@H:16]([O:15][C:14]3[CH:21]=[C:22]([F:25])[CH:23]=[CH:24][C:13]=3[Br:12])[CH2:17]2)=[N:3][N:4]=1)=[O:8])[CH3:11]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 57652823HCID 57652823, compoundHCID 68452326ethyl 5-bromo-1,3,4-oxadiazole-2-carboxylate

Product 1

HCID 68452356HCID 68452356, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of ethyl 5-bromo-1,3,4-oxadiazole-2-carboxylate (0.5 g, 2.26 mmol) and (3S)-3-(2-bromo-5-fluorophenoxy)pyrrolidine (0.5 mL, 3.4 mmol) in THF (4.5 mL) was added DBU (0.5 mL, 3.4 mmol). The mixture was stirred at room temperature for 0.5 h then filtered and the filtrate concentrated. Purification by Combiflash (SiO2, gradient elution 70-100% EtOAc/Hexanes) afforded the desired product as solid.

Workup

  1. filtrationthen filtered
  2. concentrationthe filtrate concentrated
  3. customPurification
  4. washby Combiflash (SiO2, gradient elution 70-100% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-474bdbba57574fcbae7cc94020f5b561
Source dataset
uspto-grants-2010_07
Patent number
US07754745B2

Reaction notes

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