Potassium Iodide → 5-Iodo-1,2,3,4-tetrahydro-1,8-naphthyridine

HRID 1499474

반응식

HRID 1499474 반응식
Cl[CH2:2][CH2:3][CH2:4][C:5]1[C:6](F)=[N:7][CH:8]=[CH:9][C:10]=1[I:11].[NH4+:13].[OH-].C([O-])(=O)C.[NH4+].[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CCOC(C)=O.CN(C=O)C>[I:11][C:10]1[CH:9]=[CH:8][N:7]=[C:6]2[C:5]=1[CH2:4][CH2:3][CH2:2][NH:13]2

참가 물질

8

반응물 5

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 14923Ammonium HydroxideHCID 517165Ammonium AcetateHCID 236572333-(3-Chloropropyl)-2-fluoro-4-iodopyridine

생성물 1

HCID 577562535-Iodo-1,2,3,4-tetrahydro-1,8-naphthyridine수율 69%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
60 °C

실험 절차

A mixture of 3-(3-chloropropyl)-2-fluoro-4-iodopyridine (5.0 g, 17 mmol), NH4OH (100 mL, 800 mmol), ammonium acetate (18 g, 230 mmol), potassium iodide (5.5 g, 33 mmol), potassium carbonate (12 g, 87 mmol) and DMF (26 mL) was heated at 60° C. for 8 h. The mixture allowed to cool, and diluted with EtOAc. The layers were separated and the organic layer was washed with brine, dried with MgSO4, then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using CombiFlash® apparatus, eluting with 0 to 50% EtOAc in hexanes, to give the sub-title compound (3.0 g, 69% yield). LCMS calc. for C8H10IN2(M+H)+: m/z=261.0. Found: 261.1.

후처리

  1. temperatureto cool
  2. customThe layers were separated
  3. washthe organic layer was washed with brine
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel using CombiFlash® apparatus
  7. washeluting with 0 to 50% EtOAc in hexanes

출처 및 근거

ORD 기록
ord-78e87c30a9734fc689d5da3dea89c409
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09200004B2

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