Sodium hydride → HCID 68682090, compound

HRID 1820368Notes

Reaction equation

HRID 1820368 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)=[O:12])=[CH:5]2.[H-].[Na+].FC(F)(F)S(O[CH2:27][C:28]([F:31])([F:30])[F:29])(=O)=O>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:27][C:28]([F:31])([F:30])[F:29])[C:6]([C:11]([N:13]1[CH2:14][CH2:15][O:16][CH2:17][CH2:18]1)=[O:12])=[CH:5]2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 47154711(5-bromo-1H-indole-2-yl)(morpholino)methanone

Product 1

HCID 68682090HCID 68682090, compoundYield 59.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of (5-bromo-1H-indol-2-yl)-morpholin-4-yl-methanone (6.64 g, 20 mmol) in tetrahydrofuran (60 mL) was added sodium hydride (60% dispersion in oil, 979 mg, 24 mmol) in several portions. The mixture was stirred 15 min at room temperature then 2,2,2-trifluroethyl trifluoromethanesulfonate (6.16 g, 27 mmol) was added and the reaction mixture was refluxed overnight. The reaction mixture was partitioned between ethyl acetate and an aqueous solution of sodium bicarbonate. The organic layer was washed with hydrochloric acid (1N) and brine, dried over sodium sulfate, filtered and evaporated in vacuo. The crude product was purified by flash chromatography on silica gel with dichloromethane: ethyl acetate (98:2 to 94:6 v/v) as eluant, to give 4.65 g (58%) of the desired compound as an off-white solid.

Workup

  1. temperaturethe reaction mixture was refluxed overnight
  2. customThe reaction mixture was partitioned between ethyl acetate
  3. washThe organic layer was washed with hydrochloric acid (1N) and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe crude product was purified by flash chromatography on silica gel with dichloromethane: ethyl acetate (98:2 to 94:6 v/v) as eluant

Sources & evidence

ORD record
ord-7854a16881e744b292539be08427f40a
Source dataset
uspto-grants-2009_10
Patent number
US07601711B2

Reaction notes

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