Bis(trifluoroacetoxy)iodobenzene → (S)-tert-Butyl 2-(4-(5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl)phenyl)morpholine-4-carboxylate

HRID 710241Notes

Reaction equation

HRID 710241 reaction equation
FC(F)(F)C(OI(C1C=CC=CC=1)OC(=O)C(F)(F)F)=O.[F:22][C:23]1[CH:52]=[CH:51][C:26]([C:27]([NH:29][N:30]=[CH:31][C:32]2[CH:37]=[CH:36][C:35]([C@@H:38]3[O:43][CH2:42][CH2:41][N:40]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:39]3)=[CH:34][CH:33]=2)=[O:28])=[CH:25][CH:24]=1>C(Cl)(Cl)Cl>[F:22][C:23]1[CH:24]=[CH:25][C:26]([C:27]2[O:28][C:31]([C:32]3[CH:33]=[CH:34][C:35]([C@@H:38]4[O:43][CH2:42][CH2:41][N:40]([C:44]([O:46][C:47]([CH3:48])([CH3:49])[CH3:50])=[O:45])[CH2:39]4)=[CH:36][CH:37]=3)=[N:30][N:29]=2)=[CH:51][CH:52]=1

Participants

4

Reactant 2

HCID 102317Bis(trifluoroacetoxy)iodobenzeneHCID 89689421(S)-tert-Butyl 2-(4-((2-(4-fluorobenzoyl)hydrazono)methyl)phenyl)morpholine-4-carboxylate

Product 1

HCID 131733928(S)-tert-Butyl 2-(4-(5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl)phenyl)morpholine-4-carboxylateYield 66%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

[Bis(trifluoroacetoxy)iodo]benzene (90.5 mg, 0.211 mmol) was dissolved in chloroform (5 ml), then (S)-tert-butyl 2-(4-((2-(4-fluorobenzoyl)hydrazono)methyl)phenyl)morpholine-4-carboxylate (75 mg, 0.175 mmol) was added and the mixture was stirred at room temperature for 20 min. The solvent was evaporated and the residue was purified by flash chromatography (10 g silica gel, 10 to 20% ethyl acetate in heptane) to yield a white solid (49 mg, 66%). MS (ISP): 370.1 ([M-tBu+H]+), 426.1 ([M+H]+).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by flash chromatography (10 g silica gel, 10 to 20% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-db51ece51e8949adb7c6301da7e05661
Source dataset
uspto-grants-2015_11
Patent number
US09181230B2

Reaction notes

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