Water → HCID 22038091, compound

HRID 1790400Notes

Reaction equation

HRID 1790400 reaction equation
N1CCN([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:9][CH2:8]2)CC1.Br[CH2:17][CH:18]([C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)[CH3:19].C([N:29]([CH2:32][CH3:33])[CH2:30][CH3:31])C.O.[CH3:35]N(C)C=O>>[F:26][C:23]1[CH:24]=[CH:25][C:20]([CH:18]([CH3:19])[CH2:17][N:29]2[CH2:30][CH2:31][CH:35]([N:7]3[C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[CH2:9][CH2:8]3)[CH2:33][CH2:32]2)=[CH:21][CH:22]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 8471TriethylamineHCID 2203822490561-73-2HCID 22038430HCID 22038430, compound

Product 1

HCID 22038091HCID 22038091, compound

Conditions

Temperature
60 °C

Procedure

1-(4-Piperazinyl)indoline (0.20 g) was dissolved in dimethylformamide (3 ml) and 4-(2-bromo-1-methylethyl)fluorobenzene (10.0 g) and triethylamine (0.14 ml) were added to the resultant solution followed by stirring at 60° C. overnight. After adding water, the liquid reaction mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over magnesium sulfate. After evaporating the solvent, the resulting residue was purified by NH-silica gel column chromatography (methanol/methylene chloride system) to give the title compound (178 mg) as an oil.

Workup

  1. customthe liquid reaction mixture
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customAfter evaporating the solvent
  6. customthe resulting residue was purified by NH-silica gel column chromatography (methanol/methylene chloride system)

Sources & evidence

ORD record
ord-592c2ccfeb014b6889583b5bbbafa3fb
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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