5-Benzyloxyindole → 5-Benzyloxy-3-(3-carbomethoxybenzoyl)indole

HRID 129698Notes

Reaction equation

HRID 129698 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Mg]Br.[C:21]([C:25]1[CH:26]=[C:27]([CH:31]=[CH:32][CH:33]=1)[C:28](Cl)=[O:29])([O:23][CH3:24])=[O:22]>O1CCCC1.C(OCC)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[C:12]2[C:28](=[O:29])[C:27]1[CH:31]=[CH:32][CH:33]=[C:25]([C:21]([O:23][CH3:24])=[O:22])[CH:26]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 146245-BenzyloxyindoleHCID 15563901Methyl 3-(chlorocarbonyl)benzoateHCID 178418573HCID 178418573, compound

Product 1

HCID 193722425-Benzyloxy-3-(3-carbomethoxybenzoyl)indole

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution 5-benzyloxyindole (2.23 g, 10 mmol) in 5 ml of tetrahydrofuran (THF), cooled in an external ice bath, is added dropwise with stirring 6.15 ml of a 2 molar solution of methyl magnesium bromide in diethyl ether. The resulting mixture is stirred for an additional 15 minutes in the ice bath and a solution of 3-carbmethoxybenzoyl chloride in 10 ml of THF is added dropwise. The cooling bath is removed and the reaction mixture is stirred at room temperature for 18 hours. Water is then added, followed by ethyl acetate. The layers are separated. The organic layer is dried (MgSO4) and concentrated in vacuo. The residue obtained is purified by a silica gel column, eluting with a solvent system of 25% ethyl acetate in hexane to give 5-benzyloxy-3-(3-carbomethoxybenzoyl)indole. NMR confirms this structure.

Workup

  1. additionis added dropwise
  2. customThe cooling bath is removed
  3. additionWater is then added
  4. customThe layers are separated
  5. dry with materialThe organic layer is dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue obtained
  8. customis purified by a silica gel column
  9. washeluting with a solvent system of 25% ethyl acetate in hexane

Sources & evidence

ORD record
ord-2edc6501a1ca4230900e7f76e6b0942e
Source dataset
uspto-grants-1995_11
Patent number
US05468898

Reaction notes

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