Diethyl Ether → ethyl 1-(4-chlorobenzyl)-3-methyl-1H-indole-2-carboxylate

HRID 83682Notes

Reaction equation

HRID 83682 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12].C(=O)([O-])[O-].[K+].[K+].[Cl:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27]Cl)=[CH:25][CH:24]=1.C(OCC)C>CN(C=O)C.C(OCC)(=O)C>[Cl:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27][N:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:2]([CH3:1])=[C:3]2[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 11430Potassium CarbonateHCID 593963Ethyl 3-methyl-1H-indole-2-carboxylate

Product 1

HCID 68380183ethyl 1-(4-chlorobenzyl)-3-methyl-1H-indole-2-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl 3-methyl-1H-indole-2-carboxylate (480 mg, 2.362 mmol) was dissolved in anhydrous DMF (5 mL), followed by the addition of granular potassium carbonate (408 mg, 2.95 mmol) and p-chlorobenzylchloride (0.38 mL, 2.95 mmol). The reaction was allowed to stir at 60° C. for 24 h, after which time the solution was diluted with a 1:1 solution of ethyl acetate:diethyl ether. The organic phase was washed with 10% aqueous sodium carbonate, dried with magnesium sulfate, and concentrated in vacuo. Purification was accomplished via silica gel flash chromatography (60 g silica, 10% EtOAc/hexanes) to give the title compound as a white powder. (Yield: 510 mg, 1.60 mmol, 66%) 1H NMR (400 MHz, CDCl3) 7.71, 7.34-7.15, 6.95, 5.73, 4.34, 2.63, 1.36

Workup

  1. washThe organic phase was washed with 10% aqueous sodium carbonate
  2. dry with materialdried with magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customPurification

Sources & evidence

ORD record
ord-f2c545b4280a4ce4b4b23b7f97498135
Source dataset
uspto-grants-2014_09
Patent number
US08846684B2

Reaction notes

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