Water → 3-((2-Chloropyridin-4-yl)oxy)-2-methyl-6-nitropyridine

HRID 626498노트

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HRID 626498 반응식
Br[C:2]1[C:3]([CH3:11])=[N:4][C:5]([N+:8]([O-:10])=[O:9])=[CH:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].[Cl:18][C:19]1[CH:24]=[C:23]([OH:25])[CH:22]=[CH:21][N:20]=1.O>CN(C=O)C.CCOC(C)=O>[Cl:18][C:19]1[CH:24]=[C:23]([O:25][C:2]2[C:3]([CH3:11])=[N:4][C:5]([N+:8]([O-:10])=[O:9])=[CH:6][CH:7]=2)[CH:22]=[CH:21][N:20]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 674264093-Bromo-2-methyl-6-nitropyridineHCID 178516507HCID 178516507, 화합물

생성물 1

HCID 904036213-((2-Chloropyridin-4-yl)oxy)-2-methyl-6-nitropyridine수율 55%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

A solution of 3-bromo-2-methyl-6-nitropyridine (25.59 g, 118 mmol), K2CO3 (48.9 g, 354 mmol) and 2-chloro-4-hydroxy-pyridine (30.6 g, 236 mmol) in DMF (160 mL) was sparged with Ar, heated at 100° C. overnight, then cooled to RT. The mixture was treated with water and EtOAc, the solids removed via filtration through diatomaceous earth and washed with water, EtOAc, then DCM. The aqueous filtrate was extracted with EtOAc (2×) and the organic extracts were combined with the organic filtrates, washed with water, then brine, dried over Na2SO4 and concentrated to dryness. The residue was treated with MTBE, sonicated and the resulting solid collected via filtration to afford 3-((2-chloropyridin-4-yl)oxy)-2-methyl-6-nitropyridine (17.16 g, 55%). 1H NMR (400 MHz, DMSO-d6): δ 8.38 (d, J=5.7 Hz, 1H), 8.25 (d, J=8.7 Hz, 1H), 7.95 (d, J=8.7 Hz, 1H), 7.29 (d, J=2.3 Hz, 1H), 7.16 (dd, J=5.7, 2.3 Hz, 1H), 2.46 (s, 3H); MS (ESI) m/z: 266.0 (M+H+).

후처리

  1. temperaturecooled to RT
  2. customthe solids removed via filtration through diatomaceous earth
  3. washwashed with water, EtOAc
  4. extractionThe aqueous filtrate was extracted with EtOAc (2×)
  5. washwashed with water
  6. dry with materialbrine, dried over Na2SO4
  7. concentrationconcentrated to dryness
  8. additionThe residue was treated with MTBE
  9. customsonicated
  10. filtrationthe resulting solid collected via filtration

출처 및 근거

ORD 기록
ord-f02e32c57d764a2fbea38053d6775503
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309224B2

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