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

HRID 1499474

反応式

HRID 1499474 の反応式
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

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-78e87c30a9734fc689d5da3dea89c409
出典データセット
uspto-grants-2015_12
特許番号
US09200004B2

関連ノート

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