Sodium hydride → HCID 69670750, compound

HRID 1191674Notes

Reaction equation

HRID 1191674 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[CH:5]2.[H-].[Na+].Cl[CH2:20][C:21]1[N:26]=[C:25]([C:27]([O:29][CH3:30])=[O:28])[CH:24]=[CH:23][CH:22]=1.[Cl-].[NH4+]>CN(C)C=O.C(OCC)(=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:20][C:21]1[N:26]=[C:25]([C:27]([O:29][CH3:30])=[O:28])[CH:24]=[CH:23][CH:22]=1)[C:6]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[CH:5]2

Participants

8

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 14814655-chloro-2-phenyl-1H-indoleHCID 53404482Methyl 6-(chloromethyl)pyridine-2-carboxylate

Product 1

HCID 69670750HCID 69670750, compoundYield 43.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-chloro-2-phenylindole (154 mg) in N,N-dimethylformamide (1.5 mL) was added sodium hydride (dispersed in liquid paraffin, minimum 55%, 31 mg) at room temperature, and the mixture was stirred for 15 minutes. Methyl 6-(chloromethyl)pyridine-2-carboxylate (126 mg) was added and this resulting mixture was stirred at 50 to 60° C. for additional 18 hours. Water, ethyl acetate and a saturated aqueous ammonium chloride solution were added to the reaction mixture. The organic layer was separated. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed successively with water and saturated saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by aminopropylated silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (112 mg).

Workup

  1. stirringthis resulting mixture was stirred at 50 to 60° C. for additional 18 hours
  2. customThe organic layer was separated
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic layers were washed successively with water and saturated saline
  5. dry with materialdried over anhydrous sodium 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-ba4fac05a14641eeb84c9286189379f4
Source dataset
uspto-grants-2014_03
Patent number
US08680120B2

Reaction notes

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