Dimethylformamide → HCID 66674391, compound

HRID 422108Notes

Reaction equation

HRID 422108 reaction equation
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

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 6375NitromethaneHCID 10340Sodium CarbonateHCID 66674459HCID 66674459, compound

Product 1

HCID 66674391HCID 66674391, compoundYield 83.2%

Reagents, catalysts & solvents 3

HCID 159722Silver tetrafluoroborateCatalystHCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

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]+.

Workup

  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)

Sources & evidence

ORD record
ord-726aa65046a340ffb6246ef660428db5
Source dataset
uspto-grants-2012_01
Patent number
US08101628B2

Reaction notes

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