Cesium carbonate → 2-((3-Chloro-5-fluoro-4-nitrophenoxy)methyl)-5-methylpyridine

HRID 1527726노트

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HRID 1527726 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([OH:12])[CH:5]=[C:6]([F:11])[C:7]=1[N+:8]([O-:10])=[O:9].C(=O)([O-])[O-].[Cs+].[Cs+].Cl.Cl[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][N:23]=1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([F:11])[C:7]=1[N+:8]([O-:10])=[O:9])[O:12][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][N:23]=1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 233137952-(Chloromethyl)-5-methylpyridine hydrochlorideHCID 904112693-Chloro-5-fluoro-4-nitrophenol

생성물 1

HCID 904106652-((3-Chloro-5-fluoro-4-nitrophenoxy)methyl)-5-methylpyridine수율 76%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
75 °C

실험 절차

To a mixture of 3-chloro-5-fluoro-4-nitrophenol (2.6 g, 13 mmol), cesium carbonate (8.7 g, 27 mmol), and 2-(chloromethyl)-5-methylpyridine hydrochloride (2.4 g, 13 mmol) was added DMF (88 mL) and the resulting mixture was heated to 75° Celsius for 19 h. The mixture was cooled to RT and then stirred for an additional 20 h. The resulting mixture was then partitioned between sat. NaHCO3 and EtOAc. The organic layer was separated and the aqueous layer was further extracted with EtOAc. The combined organic layers were washed with brine, dried and concentrated to dryness. The resulting residue was purified using FCC to afford the title compound (2.93 g, 74%). MS (ESI): mass calcd. for C13H10ClFN2O3, 296.04; m/z found, 297.1 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 8.45 (dd, J=1.4, 0.7, 1H), 7.55 (dd, J=7.9, 1.6, 1H), 7.32 (d, J=7.9, 1H), 6.93 (dd, J=2.5, 1.8, 1H), 6.79 (dd, J=11.1, 2.6, 1H), 5.19 (s, 2H), 2.37 (s, 3H).

후처리

  1. temperatureThe mixture was cooled to RT
  2. customThe resulting mixture was then partitioned between sat. NaHCO3 and EtOAc
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was further extracted with EtOAc
  5. washThe combined organic layers were washed with brine
  6. customdried
  7. concentrationconcentrated to dryness
  8. customThe resulting residue was purified

출처 및 근거

ORD 기록
ord-cfd862ec820e481786f0a0b2b11cca8f
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09089569B2

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