Sodium hydride → HCID 69671113, compound

HRID 1191675Notes

Reaction equation

HRID 1191675 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH:11]([CH3:13])[CH3:12])=[CH:5]2.[H-].[Na+].Cl[CH2:17][C:18]1[O:22][C:21]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:20][CH:19]=1.[Cl-].[NH4+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:17][C:18]1[O:22][C:21]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:20][CH:19]=1)[C:6]([CH:11]([CH3:13])[CH3:12])=[CH:5]2

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 263166Ethyl 5-(chloromethyl)-2-furancarboxylateHCID 225739975-Chloro-2-(propan-2-yl)-1H-indole

Product 1

HCID 69671113HCID 69671113, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-chloro-2-isopropylindole (136 mg) in N,N-dimethylformamide (2 mL) was added sodium hydride (dispersed in liquid paraffin, minimum 55%, 32 mg) under cooling with ice, and the mixture was stirred for 30 minutes. Then ethyl 5-(chloromethyl)furan-2-carboxylate (0.107 mL) was added, and the mixture was stirred at 60° C. for 20 hours. A saturated aqueous ammonium chloride solution was added to the reaction mixture and this resulting mixture was extracted with ethyl acetate. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with saturated saline, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (133 mg).

Workup

  1. temperatureunder cooling with ice
  2. stirringthe mixture was stirred at 60° C. for 20 hours
  3. extractionthis resulting mixture was extracted with ethyl acetate
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washThe combined organic layers were washed with saturated saline
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-ffa0a5b14d214e9cac2a7026393fa090
Source dataset
uspto-grants-2014_03
Patent number
US08680120B2

Reaction notes

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