Potassium Carbonate → Methyl 5-(4-benzyl-5-methoxy-4H-1,2,4-triazol-3-yl)-4-cyclopropyl-2-methylbenzoate

HRID 1487986ノート

反応式

HRID 1487986 の反応式
[CH2:1]([N:8]1[C:12]([O:13][CH3:14])=[N:11][N:10]=[C:9]1Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:16]1([C:19]2[C:28](B3OC(C)(C)C(C)(C)O3)=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[C:21]([CH3:38])[CH:20]=2)[CH2:18][CH2:17]1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O>[CH2:1]([N:8]1[C:12]([O:13][CH3:14])=[N:11][N:10]=[C:9]1[C:28]1[C:19]([CH:16]2[CH2:18][CH2:17]2)=[CH:20][C:21]([CH3:38])=[C:22]([CH:27]=1)[C:23]([O:25][CH3:26])=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 900294944-Benzyl-3-bromo-5-methoxy-4H-1,2,4-triazole2 回HCID 90030653Methyl 4-cyclopropyl-2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate2 回

生成物 1

HCID 90029805Methyl 5-(4-benzyl-5-methoxy-4H-1,2,4-triazol-3-yl)-4-cyclopropyl-2-methylbenzoate収率 89.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

A mixture of 4-benzyl-3-bromo-5-methoxy-4H-1,2,4-triazole (compound 91.3, 1.2 g, 4.48 mmol), methyl 4-cyclopropyl-2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (compound 91.1, 1.56 g, 4.93 mmol), PdCl2(dppf)CH2Cl2 (0.37 g, 0.45 mmol) and potassium carbonate (3.10 g, 22.5 mmol) in dioxane (50 mL) and water (20 mL) was degassed with argon. The mixture was heated at 90° C. for 18 hours under argon, then cooled to room temperature. The mixture was diluted with ethyl acetate (300 mL) and washed with water then brine, dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexanes:EtOAc 10:1 to 4:1) to yield 1.51 g (89%) of the title compound as thick oil. m/z (ES+) 378 (M+H)+.

後処理

  1. customwas degassed with argon
  2. temperaturecooled to room temperature
  3. additionThe mixture was diluted with ethyl acetate (300 mL)
  4. washwashed with water
  5. dry with materialbrine, dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexanes:EtOAc 10:1 to 4:1)

出典と根拠

ORDレコード
ord-281bc405bfe0464baca29d8bfcb2a785
出典データセット
uspto-grants-2016_08
特許番号
US09428502B2

反応ノート

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