Ethyl Acetate → 3-((2-Chloropyridin-4-yl)oxy)-2-ethyl-6-nitropyridine

HRID 718174노트

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HRID 718174 반응식
Br[C:2]1[C:3]([CH2:11][CH3:12])=[N:4][C:5]([N+:8]([O-:10])=[O:9])=[CH:6][CH:7]=1.[Cl:13][C:14]1[CH:19]=[C:18]([OH:20])[CH:17]=[CH:16][N:15]=1.C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>CC(N(C)C)=O>[Cl:13][C:14]1[CH:19]=[C:18]([O:20][C:2]2[C:3]([CH2:11][CH3:12])=[N:4][C:5]([N+:8]([O-:10])=[O:9])=[CH:6][CH:7]=2)[CH:17]=[CH:16][N:15]=1

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 904030533-Bromo-2-ethyl-6-nitropyridineHCID 178516507HCID 178516507, 화합물

생성물 1

HCID 904031083-((2-Chloropyridin-4-yl)oxy)-2-ethyl-6-nitropyridine수율 41.1%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

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온도
110 °C

실험 절차

3-Bromo-2-ethyl-6-nitropyridine (2.6 g, 11.3 mmol) and 2-chloro-4-hydroxypyridine (2.9 g, 22.5 mmol) were dissolved in DMA (20 mL). The solution was sonicated and sparged with Ar for 10 min. K2CO3 (4.7 g, 33.8 mmol) was added and the reaction mixture was stirred at 110° C. for 12 h. EtOAc (80 mL) was added and the suspension was washed with 10% K2CO3 (aq) (2×50 mL), 5% LiCl (aq) (2×50 mL), and brine (2×50 mL). The solution was dried (Na2SO4), concentrated in vacuo, and the resultant residue was purified by silica gel chromatography (EtOAc/hexanes) to afford 3-((2-chloropyridin-4-yl)oxy)-2-ethyl-6-nitropyridine (1.3 g, 37.2%) as a yellow oil. 1H NMR (400 MHz, DMSO-d6): δ 8.38 (d, J=5.7 Hz, 1H), 8.25 (d, J=8.7 Hz, 1H), 7.96 (d, J=8.7 Hz, 1H), 7.82 (d, J=8.6 Hz, 1H), 7.16 (dd, J=5.7, 2.3 Hz, 1H), 2.79 (q, J=7.5 Hz, 2H), 1.21 (t, J=7.5 Hz, 3H); MS (ESI) m/z: 280.0 (M+H+).

후처리

  1. customThe solution was sonicated
  2. customsparged with Ar for 10 min
  3. washthe suspension was washed with 10% K2CO3 (aq) (2×50 mL), 5% LiCl (aq) (2×50 mL), and brine (2×50 mL)
  4. dry with materialThe solution was dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customthe resultant residue was purified by silica gel chromatography (EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-80804b49ebae47f68560a677484e00d9
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09193719B2

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