Allyl bromide → 5-(1-(3-(allyloxy)benzyl)-5-methyl-1H-1,2,4-triazol-3-yl)-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole

HRID 1475245Notes

Reaction equation

HRID 1475245 reaction equation
[CH3:1][C:2]1[N:6]([CH2:7][C:8]2[CH:9]=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=2)[N:5]=[C:4]([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)[N:3]=1.Br[CH2:32][CH:33]=[CH2:34].C([O-])([O-])=O.[K+].[K+].[N+](C(C)(C)C)(C(C)(C)C)(C(C)(C)C)C(C)(C)C.[O-]S(O)(=O)=O>C(Cl)Cl.O>[CH2:34]([O:14][C:10]1[CH:9]=[C:8]([CH:13]=[CH:12][CH:11]=1)[CH2:7][N:6]1[C:2]([CH3:1])=[N:3][C:4]([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:28])[F:29])=[CH:22][CH:21]=3)[N:16]=2)=[N:5]1)[CH:33]=[CH2:32]

Participants

7

Reactant 4

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 9927882t-Bu4NHSO4HCID 86711921HCID 86711921, compound

Product 1

HCID 867119375-(1-(3-(allyloxy)benzyl)-5-methyl-1H-1,2,4-triazol-3-yl)-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazoleYield 92.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-((5-methyl-3-(3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazol-5-yl)-1H-1,2,4-triazol-1-yl)methyl)phenol (Example 59; 140 mg, 0.33 mmol) in DCM (5 mL), was added to a mixture of 3-bromoprop-1-ene (60 mg, 0.5 mmol), K2CO3 (138 mg, 1.0 mmol) and t—Bu4NHSO4 (113 mg, 0.33 mmol) in H2O (5 mL). The mixture was stirred at RT for 16 h, then diluted with H2O (50 mL) and extracted with EtOAc (3×30 mL). The combined organic layers were washed with brine (20 mL), dried over Na2SO4, filtered and concentrated under reduced pressure; the residue was purified by silica gel chromatography (Petroleum ether:EtOAc=5:1 to 2:1) to give the title compound (140 mg, 91%) as a white solid. MS (ES+) C22H18F3N5O3 requires: 457. found: 458 [M+H]+.

Workup

  1. extractionextracted with EtOAc (3×30 mL)
  2. washThe combined organic layers were washed with brine (20 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customthe residue was purified by silica gel chromatography (Petroleum ether:EtOAc=5:1 to 2:1)

Sources & evidence

ORD record
ord-20aa59f0b47b4c6aa318cdef0acfa24b
Source dataset
uspto-grants-2015_04
Patent number
US09018380B2

Reaction notes

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