Ethyl Acetate → 2-Ethyl-3-[[2-(1-methyl-1h-pyrazol-4-yl)-4-pyridinyl]oxy]-6-nitropyridine

HRID 718175ノート

反応式

HRID 718175 の反応式
Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:10]([CH2:18][CH3:19])=[N:11][C:12]([N+:15]([O-:17])=[O:16])=[CH:13][CH:14]=2)[CH:5]=[CH:4][N:3]=1.[CH3:20][N:21]1[CH:25]=[C:24](B2OC(C)(C)C(C)(C)O2)[CH:23]=[N:22]1.C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:18]([C:10]1[C:9]([O:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([C:24]3[CH:23]=[N:22][N:21]([CH3:20])[CH:25]=3)[CH:7]=2)=[CH:14][CH:13]=[C:12]([N+:15]([O-:17])=[O:16])[N:11]=1)[CH3:19]

参加物

8

反応物 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 904031083-((2-Chloropyridin-4-yl)oxy)-2-ethyl-6-nitropyridine

生成物 1

HCID 904036202-Ethyl-3-[[2-(1-methyl-1h-pyrazol-4-yl)-4-pyridinyl]oxy]-6-nitropyridine収率 102.5%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

3-((2-chloropyridin-4-yl)oxy)-2-ethyl-6-nitropyridine (1.0 g, 3.6 mmol) and 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.0 g, 4.6 mmol) were dissolved in dioxane (10 mL). A solution of K2CO3 (1.5 g, 10.6 mmol) in water (2 mL) was added and the mixture was sonicated and sparged with Ar for 10 min. Pd(PPh3)4 (0.21 g, 0.18 mmol) was added and the reaction mixture was stirred at 80° C. for 24 h. EtOAc (60 mL) was added and the mixture was washed with sat. NaHCO3 (aq) (60 mL) and brine (60 mL), dried (Na2SO4), and concentrated in vacuo to afford 2-ethyl-3-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)-6-nitropyridine (1.2 g, 100%) as a brown viscous oil that was carried forward without further purification. MS (ESI) m/z: 326.1 (M+H+).

後処理

  1. customthe mixture was sonicated
  2. customsparged with Ar for 10 min
  3. washthe mixture was washed with sat. NaHCO3 (aq) (60 mL) and brine (60 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-b84a06c9186246de9ce80d8f05923dd7
出典データセット
uspto-grants-2015_11
特許番号
US09193719B2

反応ノート

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