Sodium hydride → 1-(2-fluoroethyl)-4-iodo-1H-pyrazole

HRID 2220447Notes

Reaction equation

HRID 2220447 reaction equation
[I:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.[H-].[Na+].I[CH2:10][CH2:11][F:12]>CN(C=O)C>[F:12][CH2:11][CH2:10][N:4]1[CH:3]=[C:2]([I:1])[CH:6]=[N:5]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 69804Ethane, 1-fluoro-2-iodo-HCID 770224-Iodopyrazole

Product 1

HCID 597727061-(2-fluoroethyl)-4-iodo-1H-pyrazoleYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-iodo-1H-pyrazole (1.10 g, 5.7 mmol) in anhydrous DMF (25 mL) is treated with NaH (0.23 g, 60% in mineral oil, 5.7 mmol). After stirring for 20 minutes at room temperature, the reaction mixture is treated with 1-iodo-2-fluoroethane (1.0 g, 5.7 mmol) and stirred over night at room temperature. The reaction is quenched with H2O and diluted with EtOAc. The two layers are separated and the aqueous is extracted with EtOAc. The combined organic extracts are washed with H2O, brine, dried (Na2SO4) and concentrated. The crude material is purified by chromatography (silica gel, EtOAc/hexane: 15/85) to afford the title compound (1.08 g, 79%) as an oil. MS (+) ES 240 (M+H)+.

Workup

  1. stirringstirred over night at room temperature
  2. customThe reaction is quenched with H2O
  3. additiondiluted with EtOAc
  4. customThe two layers are separated
  5. extractionthe aqueous is extracted with EtOAc
  6. washThe combined organic extracts are washed with H2O, brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customThe crude material is purified by chromatography (silica gel, EtOAc/hexane: 15/85)

Sources & evidence

ORD record
ord-28c6b807956346a28496b63957a9dcbc
Source dataset
uspto-grants-2008_08
Patent number
US07417047B2

Reaction notes

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