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Acetonitrile → 5-difluoromethyl-4-{5-(3-ethyl-3-methoxy-1-pentynyl)-2-methylbenzyl)-2-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 1883625
ノート
印刷プレビュー

反応式

HRID 1883625 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]([CH3:19])=[C:6]([CH:18]=1)[CH2:7][N:8]1[C:12]([CH:13]([F:15])[F:14])=[N:11][N:10]([CH3:16])[C:9]1=[O:17].[CH2:20]([C:22]([O:27][CH3:28])([CH2:25][CH3:26])[C:23]#[CH:24])[CH3:21].C(N(CC)CC)C.C(#N)C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu](I)I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.COC(C)(C)C>[F:14][CH:13]([F:15])[C:12]1[N:8]([CH2:7][C:6]2[CH:18]=[C:2]([C:21]#[C:20][C:22]([CH2:25][CH3:26])([O:27][CH3:28])[CH2:23][CH3:24])[CH:3]=[CH:4][C:5]=2[CH3:19])[C:9](=[O:17])[N:10]([CH3:16])[N:11]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 5660771-Pentyne, 3-ethyl-3-methoxy-HCID 129940064-(5-bromo-2-methylbenzyl)-5-difluoromethyl-2-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one2 回

生成物 1

HCID 235082285-difluoromethyl-4-{5-(3-ethyl-3-methoxy-1-pentynyl)-2-methylbenzyl)-2-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one収率 84.5%

試薬・触媒・溶媒

4
HCID 11776Triphenylphosphine触媒HCID 83717Copper iodide触媒HCID 178418476HCID 178418476、化合物触媒HCID 15413tert-Butyl methyl ether溶媒

実験手順

332 mg (1.00 mmol) of 4-(5-bromo-2-methylbenzyl)-5-difluoromethyl-2-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one (Compound 40), 378 mg (3.00 mmol) of 3-ethyl-3-methoxy-1-pentine, 14 mg (0.020 mmol) of PdCl2(PPh3)2, 9.5 mg (0.050 mmol) of copper iodide (I), 15.7 mg (0.060 mmol) of triphenylphosphine and 0.5 ml of triethylamine were added to 4.0 ml of acetonitrile, and the mixture was heated under reflux for 5 hours in nitrogen atmosphere. After cooling to room temperature, t-butyl methyl ether was added to the reaction solution, and the mixture was washed with water and dried over anhydrous magnesium sulfate, then, concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (eluant: hexane/ethyl acetate=2/1 (v/v)), to obtain 319 mg of 5-difluoromethyl-4-{5-(3-ethyl-3-methoxy-1-pentynyl)-2-methylbenzyl}-2-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one (Compound 277).

後処理

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 hours in nitrogen atmosphere
  3. washthe mixture was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-f5ccff407d1c4cce9bfac854c4df7d41
出典データセット
uspto-grants-2004_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06762197B2

反応ノート

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