Potassium Iodide → Ethyl 5-acetoxy-N-(3-methoxy-4-chlorobenzyl)indole-2-carboxylate

HRID 1610928Notes

Reaction equation

HRID 1610928 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:8]2)(=[O:3])[CH3:2].[H-].[Na+].[I-].[K+].[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][C:32]=1[Cl:33])[CH2:28]Br>CN(C=O)C>[C:1]([O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH2:28][C:27]1[CH:30]=[CH:31][C:32]([Cl:33])=[C:25]([O:24][CH3:23])[CH:26]=1)[C:9]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:8]2)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 24758Sodium hydrideHCID 11379620Ethyl 5-acetoxyindole-2-carboxylateHCID 136628594-(Bromomethyl)-1-chloro-2-methoxybenzene

Product 1

HCID 22259373Ethyl 5-acetoxy-N-(3-methoxy-4-chlorobenzyl)indole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of ethyl 5-acetoxyindole-2-carboxylate (283 mg) in DMF (6 ml) was added sodium hydride (54 mg, 60% dispersion in oil). The mixture was stirred for 30 minutes, a catalytic amount of potassium iodide and a solution of 3-methoxy-4-chlorobenzyl bromide (345 mg) in DMF (2 ml) was added. The mixture was stirred for 2 hours, quenched with water and extracted with ethyl acetate. The organic extracts were dried, evaporated and the resulting gum was purified by column chromatography elutig with 20% ethyl acetate/isohexane to give the desired product as an oil which solidified on standing (310 mg, 63%). NMR (CDCl3): d 1.4 (t, 3H), 2.3 (s, 3H), 3.8 (s, 3H), 4.35 (q, 2H, 5.8 (s, 2H), 6.5 (dd, 1H), 6.7 (d, 1H), 7.05 (dd, 1H), 7.2-7.4 (m, 4H); m/z 402 (M+H+).

Workup

  1. stirringThe mixture was stirred for 2 hours
  2. customquenched with water
  3. extractionextracted with ethyl acetate
  4. customThe organic extracts were dried
  5. customevaporated
  6. customthe resulting gum was purified by column chromatography elutig with 20% ethyl acetate/isohexane

Sources & evidence

ORD record
ord-8a9a7a9ff6c64ce99388c622b7019f0d
Source dataset
uspto-grants-2006_01
Patent number
US06984657B1

Reaction notes

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