N-(4-(3-bromophenyl)-3-oxobutan-2-yl)-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole-5-carboxamide → 3-(4-(Trifluoromethoxy)phenyl)-1,2,4-oxadiazole

HRID 517537Notes

Reaction equation

HRID 517537 reaction equation
BrC1C=C(CC(=O)C(NC([C:15]2[O:19][N:18]=[C:17]([C:20]3[CH:25]=[CH:24][C:23]([O:26][C:27]([F:30])([F:29])[F:28])=[CH:22][CH:21]=3)[N:16]=2)=O)C)C=CC=1>O=P(Cl)(Cl)Cl>[F:30][C:27]([F:28])([F:29])[O:26][C:23]1[CH:22]=[CH:21][C:20]([C:17]2[N:16]=[CH:15][O:19][N:18]=2)=[CH:25][CH:24]=1

Participants

3

Reactant 1

HCID 86711479N-(4-(3-bromophenyl)-3-oxobutan-2-yl)-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole-5-carboxamide

Product 1

HCID 547723813-(4-(Trifluoromethoxy)phenyl)-1,2,4-oxadiazoleYield 108.6%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

A solution of N-(4-(3-bromophenyl)-3-oxobutan-2-yl)-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole-5-carboxamide (200 mg, 0.4 mmol) in POCl3 (5 mL) was stirred at 110° C. for 5 h, cooled to RT, concentrated, and neutralized with aqueous K2CO3 (˜8M). The residue was diluted with H2O, and extracted with EtOAc. The combined organic layers were washed with H2O and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by prep-TLC (Petroleum ether:EtOAc=5:1) to afford 545-(3-bromobenzyl)-4-methyloxazol-2-yl)-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole (100 mg, 52%) as a white solid. MS (ES+) C20H13BrF3N2O2 requires: 479, 481, found: no desired peak; 1H NMR (500 MHz, CDCl3) δ 8.23 (d, J=9.0 Hz, 2H), 7.42-7.31 (m, 4H), 7.23-7.

Workup

  1. concentrationconcentrated
  2. additionThe residue was diluted with H2O
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with H2O and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by prep-TLC (Petroleum ether:EtOAc=5:1)

Sources & evidence

ORD record
ord-90c9a95e63524270b1762b998aa2cf6c
Source dataset
uspto-grants-2015_08
Patent number
US09115120B2

Reaction notes

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