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 1475245노트

반응식

HRID 1475245 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매2회HCID 6344Dichloromethane용매

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-20aa59f0b47b4c6aa318cdef0acfa24b
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09018380B2

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