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 1475245ノート

反応式

HRID 1475245 の反応式
[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]

参加物

7

反応物 4

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 9927882t-Bu4NHSO4HCID 86711921HCID 86711921、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 6344Dichloromethane溶媒

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-20aa59f0b47b4c6aa318cdef0acfa24b
出典データセット
uspto-grants-2015_04
特許番号
US09018380B2

反応ノート

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