5-Benzyloxyindole → Ethyl 2-(5-benzyloxyindolyl)cyclopropanecarboxylate

HRID 1295107Notes

Reaction equation

HRID 1295107 reaction equation
[H-].[Na+].[CH2:3]([O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[CH:14]2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Br[CH:21]1[CH2:23][CH:22]1[C:24]([O:26][CH2:27][CH3:28])=[O:25]>CN(C)C=O>[CH2:3]([O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][C:15]([CH:21]1[CH2:23][CH:22]1[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:14]2)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 146245-BenzyloxyindoleHCID 24758Sodium hydrideHCID 22570347Ethyl 2-bromocyclopropanecarboxylate

Product 1

HCID 22570370Ethyl 2-(5-benzyloxyindolyl)cyclopropanecarboxylateYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of NaH (0.355 g, 14.0 mmol) in 100 ml of dry N,N-dimethylformamide was added slowly 5-benzyloxyindole (3.0 g, 13.4 mmol). When the evolution of H2 ceased, ethyl 2-bromocyclopropanecarboxylate(2.85 g, 0.0148 mol), as prepared in the preceding step, was added to the mixture and the reaction was refluxed for a period of 17 h under argon. Then the reaction was cooled down at ambient temperature and quenched carefully with water. After evaporation of the solvent under vacuum, the crude product was purified by flash chromatography on silica gel to obtain the title compound (3.45 g, 77%). 1H NMR (400 MHz, CDCl3) δ 1.34 (t, 3H, J=7.1 Hz), 1.62 (m, 1H), 1.73 (m, 1H), 2.14 (m, 1H), 3.78 (m, 1H), 4.24 (c, 2H, J=7.1 Hz), 5.10 (s, 2H), 6.36 (dd, 1H, J=0.7, 3.2 Hz), 6.98 (dd, 1H, J=2.4, 8.8 Hz), 7.04 (d, 1H, J=3.2 Hz), 7.14 (d, 1H, J=2.4 Hz), 7.38 (m, 4H), 7.45 (m, 2H).

Workup

  1. additionwas added to the mixture
  2. temperaturethe reaction was refluxed for a period of 17 h under argon
  3. customquenched carefully with water
  4. customAfter evaporation of the solvent under vacuum
  5. customthe crude product was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-3669a153d9f842f7acc71c8274c3c303
Source dataset
uspto-grants-2007_07
Patent number
US07241789B2

Reaction notes

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