Ethanol → HCID 66674186, compound

HRID 422109Notes

Reaction equation

HRID 422109 reaction equation
C(N(S(F)(F)[F:7])CC)C.[F:10][C:11]1[N:16]=[CH:15][C:14]([CH2:17]O)=[C:13]([I:19])[CH:12]=1.C(O)C.C(=O)(O)[O-].[Na+]>ClCCl>[F:10][C:11]1[CH:12]=[C:13]([I:19])[C:14]([CH2:17][F:7])=[CH:15][N:16]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 66674391HCID 66674391, compound

Product 1

HCID 66674186HCID 66674186, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add diethylaminosulfur trifluoride (892 mg, 4 mmol) drop-wise to a solution of (6-fluoro-4-iodo-pyridin-3-yl)-methanol in dichloromethane (25 mL) in a round bottom flask under nitrogen, and then add ethanol (0.3 mL) at 0-5° C. Stir the mixture for 3 hours. Pour the reaction mixture into saturated sodium bicarbonate solution. Abstract the product into 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 (10% methanol in dichloromethane) to give the title compound (0.32 g, 53%). MS (ES) m/z 256 [M+1]+.

Workup

  1. customat 0-5° C
  2. washAbstract the product into chloroform, and wash 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 a crude product
  8. customPurify the crude with flash column chromatography (10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-0085cc55ecc041b1b1c8b583fdc5d82e
Source dataset
uspto-grants-2012_01
Patent number
US08101628B2

Reaction notes

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