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

HRID 561008ノート

反応式

HRID 561008 の反応式
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]

参加物

5

反応物 2

HCID 33557Sodium AzideHCID 66674459HCID 66674459、化合物

生成物 1

HCID 866404905-Azidomethyl-2-fluoro-4-iodo-pyridine収率 82%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 6228Dimethylformamide溶媒

実験手順

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]+

後処理

  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)

出典と根拠

ORDレコード
ord-92ab2a9985944f2994d071ea3e6e62a5
出典データセット
uspto-grants-2011_11
特許番号
US08063212B2

反応ノート

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