Dimethylformamide → HCID 66674391、化合物

HRID 422108ノート

反応式

HRID 422108 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+](C)([O-])=[O:12].CN(C)C=O.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)(Cl)Cl.F[B-](F)(F)F.[Ag+].CO>[F:9][C:6]1[N:7]=[CH:8][C:3]([CH2:2][OH:12])=[C:4]([I:10])[CH:5]=1

参加物

8

反応物 4

HCID 6228DimethylformamideHCID 6375NitromethaneHCID 10340Sodium CarbonateHCID 66674459HCID 66674459、化合物

生成物 1

HCID 66674391HCID 66674391、化合物収率 83.2%

試薬・触媒・溶媒 3

HCID 159722Silver tetrafluoroborate触媒HCID 887Methanol溶媒HCID 6212Chloroform溶媒

実験手順

Combine 5-bromomethyl-2-fluoro-4-iodo-pyridine (0.9 g, 2.85 mmol), nitromethane (15 mL, 278 mmol), silver tetrafluoroborate (721 mg, 3.7 mmol), and dimethylformamide (5 mL) in a round bottom flask. Stir the mixture overnight at room temperature. Add sodium carbonate (1.81 g, 17.1 mmol) and methanol (10 mL) into the mixture. Stir at room temperature for another 4 hours. 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 the crude product. Purify the crude with flash column chromatography (eluted with 10% methanol in dichloromethane) to give the desired product (0.6 g, 83%). MS (ES) m/z 254 [M+1]+.

後処理

  1. stirringStir at room temperature for another 4 hours
  2. washwash with water and saturated aqueous sodium chloride
  3. customSeparate the organic layer from the aqueous layer
  4. dry with materialdry over MgSO4
  5. filtrationAfter filtration
  6. customevaporate the organic solvent in vacuo
  7. customto give the crude product
  8. customPurify the crude
  9. washwith flash column chromatography (eluted with 10% methanol in dichloromethane)

出典と根拠

ORDレコード
ord-726aa65046a340ffb6246ef660428db5
出典データセット
uspto-grants-2012_01
特許番号
US08101628B2

反応ノート

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