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

HRID 1049247ノート

反応式

HRID 1049247 の反応式
[CH3:1][N:2]1[CH:6]=[C:5](B2OC(C)(C)C(C)(C)O2)[CH:4]=[N:3]1.Cl[C:17]1[CH:22]=[C:21]([O:23][C:24]2[C:25]([CH2:33][CH3:34])=[N:26][C:27]([N+:30]([O-:32])=[O:31])=[CH:28][CH:29]=2)[CH:20]=[CH:19][N:18]=1.C([O-])([O-])=O.[K+].[K+]>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>[CH2:33]([C:25]1[C:24]([O:23][C:21]2[CH:22]=[CH:17][N:18]=[C:19]([C:5]3[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=3)[CH:20]=2)=[CH:29][CH:28]=[C:27]([N+:30]([O-:32])=[O:31])[N:26]=1)[CH3:34]

参加物

7

反応物 3

HCID 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 100%

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

A mixture of 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (863 mg, 4.15 mmol), 3-((2-chloropyridin-4-yl)oxy)-2-ethyl-6-nitropyridine (892 mg, 3.19 mmol), K2CO3 (1.322 mg, 9.57 mmol) and Pd(PPh3)4 (184 mg, 0.159 mmol) in dioxane (6 mL) and water (1.5 mL) was sparged with Ar, heated at 80° C. for 24 h, then cooled to RT and stirred for 24 h. The mixture was treated with EtOAc, washed with satd. NaHCO3 (1×), then brine (1×), dried over Na2SO4 and concentrated to dryness to afford 2-ethyl-3-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)-6-nitropyridine (100% yield assumed) as a thick oil. Material carried on to the next step without purification. MS (ESI) m/z: 326.1 (M+H+).

後処理

  1. customwas sparged with Ar
  2. temperaturecooled to RT
  3. additionThe mixture was treated with EtOAc
  4. washwashed with satd
  5. dry with materialNaHCO3 (1×), then brine (1×), dried over Na2SO4
  6. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-274efb2cc31347cbb6f6c1b438c2bb2f
出典データセット
uspto-grants-2016_07
特許番号
US09382228B2

反応ノート

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