Dimethylformamide → HCID 86755281, compound

HRID 1003583Notes

Reaction equation

HRID 1003583 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[C:11]1[CH2:12][CH2:13][N:14]([CH3:17])[CH2:15][CH:16]=1.[H-].[K+].C([Li])(C)(C)C.CN(C)[CH:27]=[O:28]>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[C:11]1[CH2:12][CH2:13][N:14]([CH3:17])[CH2:15][CH:16]=1.[CH:27]([C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[C:11]1[CH2:12][CH2:13][N:14]([CH3:17])[CH2:15][CH:16]=1)=[O:28]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 82127Potassium hydrideHCID 149732085-bromo-3-(1-methyl-1,2,3,6-tetrahydro-4-pyridinyl)-1H-indoleHCID 178418306HCID 178418306, compound

Product 1

HCID 86755281HCID 86755281, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of 10.0 gm (34.3 mMol) 5-bromo-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole in 150 mL tetrahydrofuran was added dropwise to a stirring suspension of 7.2 gm (36 mMol) potassium hydride in 150 mL tetrahydrofuran at 0° C. After 30 minutes, the reaction mixture is cooled to -78° C. and to it was added 44.5 mL (75.6 mMol) of a precooled (-78° C.) solution of tert-butyllithium (1.7 M in tetrahydrofuran) via cannula. After 15 minutes 4.0 mL (51.5 mL) dimethylformamide was added via cannula and the reaction mixture was allowed to warm slowly to room temperature. The reaction mixture was quenched by the addition of 5N sodium hydroxide and the reaction mixture extracted well with diethyl ether. The organic extracts were combined, washed with saturated aqueous sodium chloride and concentrated under reduced pressure. The resulting residue was subjected to silica gel chromatography, eluting with 4% methanol in dichloromethane. Fractions shown to contain product were combined and concentrated under reduced pressure to provide 3.8 gm (46%) of the title compound as a light yellow solid.

Workup

  1. temperatureto warm slowly to room temperature
  2. customThe reaction mixture was quenched by the addition of 5N sodium hydroxide
  3. extractionthe reaction mixture extracted well with diethyl ether
  4. washwashed with saturated aqueous sodium chloride
  5. concentrationconcentrated under reduced pressure
  6. washeluting with 4% methanol in dichloromethane
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f562820d6a36493fb0486398700f14ba
Source dataset
uspto-grants-2000_04
Patent number
US06046215

Reaction notes

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