Sodium hydride → HCID 86707947, compound

HRID 2400295Notes

Reaction equation

HRID 2400295 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]1([CH3:15])[CH2:14][CH2:13]1)=[CH:6]2.[H-].[Na+].Cl[CH2:19][C:20]1[O:24][C:23]([C:25]#[N:26])=[CH:22][CH:21]=1.[Cl-].[NH4+]>CN(C)C=O.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:19][C:20]1[O:24][C:23]([C:25]#[N:26])=[CH:22][CH:21]=1)[C:7]([C:12]1([CH3:15])[CH2:13][CH2:14]1)=[CH:6]2

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 13546956HCID 13546956, compoundHCID 86707948HCID 86707948, compound

Product 1

HCID 86707947HCID 86707947, compoundYield 14.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 5-methoxy-2-(1-methylcyclopropyl)-1H-indole (155 mg) in N,N-dimethylformamide (3 mL) was added sodium hydride (dispersed in liquid paraffin, 50% or more, 39 mg) under ice-cooling. This mixture was stirred at room temperature for 50 minutes. Subsequently, a solution of 5-chloromethylfuran-2-carbonitrile (131 mg) in N,N-dimethylformamide (0.5 mL) was added thereto at room temperature, and the mixture was stirred at 80° C. for 14 hours. To the reaction mixture were added saturated aqueous ammonium chloride solution and water, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine successively, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by aminopropylated silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (34 mg). 1H-NMR (CDCl3) δ ppm: 0.70-1.00 (4H, m), 1.35 (3H, s), 3.83 (3H, s), 5.45 (2H, s), 5.95-6.00 (1H, m), 6.20-6.30 (1H, m), 6.75-6.85 (1H, m), 6.90-7.10 (3H, m).

Workup

  1. temperaturecooling
  2. stirringat room temperature, and the mixture was stirred at 80° C. for 14 hours
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine successively
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by aminopropylated silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-3c6eec45aa144225b8cc7cc04859442a
Source dataset
uspto-grants-2014_08
Patent number
US08796247B2

Reaction notes

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