Sodium Azide → 5-Azidomethyl-2-fluoro-4-iodo-pyridine

HRID 561008노트

반응식

HRID 561008 반응식
Br[CH2:2][C:3]1[C:4]([I:10])=[CH:5][C:6]([F:9])=[N:7][CH:8]=1.[N-:11]=[N+:12]=[N-:13].[Na+]>CN(C)C=O.C(Cl)(Cl)Cl>[N:11]([CH2:2][C:3]1[C:4]([I:10])=[CH:5][C:6]([F:9])=[N:7][CH:8]=1)=[N+:12]=[N-:13]

참가 물질

5

반응물 2

HCID 33557Sodium AzideHCID 66674459HCID 66674459, 화합물

생성물 1

HCID 866404905-Azidomethyl-2-fluoro-4-iodo-pyridine수율 82%

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 6228Dimethylformamide용매

실험 절차

Combine 5-bromomethyl-2-fluoro-4-iodo-pyridine (0.45 g, 1.4 mmol), sodium azide (370 mg, 5.7 mmol), and 18-crown ether (45 mg, 0.17 mml) in dimethylformamide (10 mL) in a round bottom flask. Stir the mixture for 4 hours at room temperature. Dilute the reaction mixture with chloroform, and wash with water and saturated aqueous sodium chloride. Separate the organic layer from the aqueous layer and dry over MgSO4. After filtration, evaporate the organic solvent in vacuo to give a crude product. Purify the crude with flash column chromatography (eluted with 20% methyl acetate in hexane) to give the title compound (colorless oil, 0.0.32 g, 82%). MS (ES) m/z 279 [M+1]+

후처리

  1. washwash with water and saturated aqueous sodium chloride
  2. customSeparate the organic layer from the aqueous layer
  3. dry with materialdry over MgSO4
  4. filtrationAfter filtration
  5. customevaporate the organic solvent in vacuo
  6. customto give a crude product
  7. customPurify the crude
  8. washwith flash column chromatography (eluted with 20% methyl acetate in hexane)

출처 및 근거

ORD 기록
ord-92ab2a9985944f2994d071ea3e6e62a5
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063212B2

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