Sodium hydride → HCID 49780332, compound

HRID 402309Notes

Reaction equation

HRID 402309 reaction equation
[C:1]1([CH3:16])[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[NH:12][CH:11]=[CH:10]3)[CH:2]=1.[H-].[Na+].Br[C:20]1[CH:21]=[C:22]2[C:26](=CC=1)N(CCCCCCCC)C=[C:23]2CC(O)=O>O>[CH3:23][C:22]([CH3:26])=[CH:21][CH2:20][N:12]1[C:13]2[C:9](=[CH:8][C:7]([C:3]3[CH:2]=[C:1]([CH3:16])[CH:6]=[CH:5][CH:4]=3)=[CH:15][CH:14]=2)[CH:10]=[CH:11]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 20100022HCID 20100022, compoundHCID 49782539HCID 49782539, compound

Product 1

HCID 49780332HCID 49780332, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the solution of 5-m-tolyl-1H-indole (3, 4 mmol, 1 equiv.) in anhydrous dimethylsulfoxide(DMSO) was added NaH (60% in mineral oil dispersion, 4.8 mmol, 1.2 equiv.) at room temperature. The mixture was stirred for about 1 h at the same temperature, then 1-chloro-3-methylbut-2-ene (4, 4.8 mmol, 1.2 equiv.) was added and the mixture was stirred for 4 h. Water was added to stop the reaction. The mixture was extracted by dichloromethane and the organic layer was washed with brine, dried (Na2SO4), filtered, and evaporated. The residue was purified by column chromatography of silica gel to get off-yellow oil. Yield: 87.1%. 1H NMR (300 MHz, CDCl3): δ 1.82 (s, 3 H), 1.88 (s, 3 H), 2.48 (s, 3 H), 4.74 (d, J=6.6 Hz, 2 H), 5.45 (t, J=6.9 Hz, 1 H), 6.57 (d, J=2.4 Hz, 1 H), 7.17 (t, J=3.3 Hz, 2 H), 7.34-7.43 (m, 2H), 7.49-7.52 (m, 3H), 7.89 (s, 1H). 13C NMR (75 MHz, CDCl3) δ 18.0, 21.6, 25.6, 44.2, 101.3, 109.6, 119.4, 119.9, 121.2, 124.4, 126.9, 128.0, 128.2, 128.5, 129.2, 132.9, 135.5, 136.3, 138.1, 142.6.

Workup

  1. stirringthe mixture was stirred for 4 h
  2. customthe reaction
  3. extractionThe mixture was extracted by dichloromethane
  4. washthe organic layer was washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography of silica gel
  9. customto get off-yellow oil

Sources & evidence

ORD record
ord-5991d757a1dd473fb238459c7085051a
Source dataset
uspto-grants-2014_06
Patent number
US08742100B2

Reaction notes

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