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

HRID 2278897노트

반응식

HRID 2278897 반응식
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]

참가 물질

8

반응물 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

생성물 1

HCID 904036202-Ethyl-3-[[2-(1-methyl-1h-pyrazol-4-yl)-4-pyridinyl]oxy]-6-nitropyridine수율 100%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 312751,4-Dioxane용매

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온도
80 °C

실험 절차

A mixture of Example A8 (1.10 g, 3.93 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.06 g, 5.11 mmol), K2CO3 (1.631 g, 11.80 mmol) and Pd(PPh3)4 (227 mg, 0.197 mmol) in dioxane (8 mL) and water (2 mL) was sparged with Ar and heated at 80° C. for 24 h. The mixture was cooled to RT, treated with EtOAc, washed with satd. NaHCO3, then brine, dried over Na2SO4 and concentrated to dryness to afford crude 2-ethyl-3-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)-6-nitropyridine (100% yield assumed) without further purification. MS (ESI) m/z: 326.1 (M+H+).

후처리

  1. temperatureThe mixture was cooled to RT
  2. washwashed with satd
  3. dry with materialNaHCO3, then brine, dried over Na2SO4
  4. concentrationconcentrated to dryness

출처 및 근거

ORD 기록
ord-87378e23724f4acca452a8f83677870d
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09133183B2

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