Cesium carbonate → 4-(4-{[3-(ethyloxy)phenyl]oxy}phenyl)-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 1484523

反応式

HRID 1484523 の反応式
C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:7]([O:9][C:10]1[CH:11]=[C:12]([OH:16])[CH:13]=[CH:14][CH:15]=1)[CH3:8].Br[C:18]1[CH:23]=[CH:22][C:21]([N:24]2[C:28]([CH3:29])=[N:27][NH:26][C:25]2=[O:30])=[CH:20][CH:19]=1.CC(C)(C(=O)CC(=O)C(C)(C)C)C>CN1C(=O)CCC1.[Cu](Cl)Cl>[CH2:7]([O:9][C:10]1[CH:11]=[C:12]([O:16][C:18]2[CH:19]=[CH:20][C:21]([N:24]3[C:28]([CH3:29])=[N:27][NH:26][C:25]3=[O:30])=[CH:22][CH:23]=2)[CH:13]=[CH:14][CH:15]=1)[CH3:8]

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 693063-EthoxyphenolHCID 707002,2,6,6-Tetramethyl-3,5-heptanedioneHCID 14877914-(4-bromophenyl)-3-methyl-4,5-dihydro-1H-1,2,4-triazol-5-one2 回

生成物 1

HCID 900239604-(4-{[3-(ethyloxy)phenyl]oxy}phenyl)-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one収率 6.6%

試薬・触媒・溶媒 2

HCID 24014Cupric Chloride触媒HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

To cesium carbonate (641 mg, 1.968 mmol, 2 equiv) was added 3-ethoxyphenol (272 mg, 1.968 mmol, 2 equiv) in 4 mL of NMP. The reaction mixture was degassed and filled with nitrogen 3 times (3 cycles vacuum/nitrogen). 4-(4-bromophenyl)-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one (Intermediate 22, 250 mg, 0.984 mg, 1 equiv), 2,2,6,6-tetramethyl-3,5-heptanedione (18 mg, 0.098 mmol, 0.1 equiv) and copper chloride (58 mg, 0.590 mmol, 0.6 equiv) were added. The reaction mixture was degassed and filled with nitrogen 3 times (3 cycles vacuum/nitrogen) and then warmed to 120 C under nitrogen overnight. The reaction mixture was diluted with dichloromethane and filtered. Volatiles were removed in vacuo and the residue was purified by preparative HPLC to give the title compound (20.2 mg).

後処理

  1. customThe reaction mixture was degassed
  2. additionfilled with nitrogen 3 times (3 cycles vacuum/nitrogen)
  3. customThe reaction mixture was degassed
  4. additionfilled with nitrogen 3 times (3 cycles vacuum/nitrogen)
  5. temperaturewarmed to 120 C under nitrogen overnight
  6. additionThe reaction mixture was diluted with dichloromethane
  7. filtrationfiltered
  8. customVolatiles were removed in vacuo
  9. customthe residue was purified by preparative HPLC

出典と根拠

ORDレコード
ord-2ac0da37bd484d5bae3e0c3966ac3876
出典データセット
uspto-grants-2016_08
特許番号
US09422252B2

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