Sodium hydride → HCID 69058159, compound

HRID 1817499Notes

Reaction equation

HRID 1817499 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]([C:11]2[C:19]3[C:14](=[C:15]([C:20]([F:23])([F:22])[F:21])[CH:16]=[CH:17][CH:18]=3)[NH:13][N:12]=2)=[O:10])[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].I[CH2:27][CH2:28][CH3:29]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]([C:11]2[C:19]3[C:14](=[C:15]([C:20]([F:23])([F:21])[F:22])[CH:16]=[CH:17][CH:18]=3)[N:13]([CH2:27][CH2:28][CH3:29])[N:12]=2)=[O:10])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 178490436HCID 178490436, compound

Product 1

HCID 69058159HCID 69058159, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of [3-(methoxy)phenyl](7-trifluoromethyl-1H-indazol-3-yl)methanone (0.27 g, 0.85 mmol) in 5 mL DMF was added in one portion sodium hydride (0.034 g, 0.85 mmol, 60% in oil). After the gas evolution ceased, 1-iodopropane (0.097 mL, 1.0 mmol) was added and the reaction was stirred at ambient to 50° C. for 24 hours. The cool reaction mixture was partitioned with EtOAc and 1 N HCl. The organic phase was washed with brine and dried (Na2SO4). Removal of the solvent in vacuo afforded the crude product which was purified by flash chromatography (silica gel, hexane/EtOAC, 9:1) to give the title compound (0.262 g) as an oil. MS (ESI) m/z 363 ([M+H]+);

Workup

  1. customThe cool reaction mixture
  2. customwas partitioned with EtOAc and 1 N HCl
  3. washThe organic phase was washed with brine
  4. dry with materialdried (Na2SO4)
  5. customRemoval of the solvent in vacuo
  6. customafforded the crude product which
  7. customwas purified by flash chromatography (silica gel, hexane/EtOAC, 9:1)

Sources & evidence

ORD record
ord-4924126e79414da4ac9fa023459c58ae
Source dataset
uspto-grants-2009_10
Patent number
US07598286B2

Reaction notes

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