6-Iodo-2,3-dimethoxypyridine → 5,6-Dimethoxypicolinonitrile

HRID 1675961노트

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HRID 1675961 반응식
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[C:5](I)[N:4]=1.[Cu](C#N)[C:13]#[N:14]>CN(C=O)C>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[C:5]([C:13]#[N:14])[N:4]=1

참가 물질

4

반응물 2

HCID 453617466-Iodo-2,3-dimethoxypyridineHCID 178418260HCID 178418260, 화합물

생성물 1

HCID 467367605,6-Dimethoxypicolinonitrile

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
150 °C

실험 절차

To a solution of 2,3-dimethoxy-6-iodopyridine (11-4, 24.0 g, 91 mmol) in DMF (181 mL) was added copper cyanide (9.73 g, 109 mmol) and heated to 150° C. for 20 minutes in a microwave reactor. The mixture was partitioned between water and EtOAc. The organic phase was washed with brine, dried over Na2SO4, filtered and concentrated. The crude material was purified by gradient elution on silica gel (0 to 40% EtOAc in hexanes) to yield the desired product (11-5) as an off-white crystalline powder. ESI+MS [M+H]+ C8H8N2O2: 165.0 found, 165.1 required.

후처리

  1. customThe mixture was partitioned between water and EtOAc
  2. washThe organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by gradient elution on silica gel (0 to 40% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-70b6e6bc30d64d6c9617158e7dff3903
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08003797B2

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