3,4-Dichlorobenzyl chloride → Ethyl 3-formyl-N-(3,4-dichlorobenzyl)indole-2-carboxylate

HRID 2307919Notes

Reaction equation

HRID 2307919 reaction equation
[H-].[Na+].[CH:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:4].[Cl:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=1[Cl:28])[CH2:23]Cl>CN(C=O)C>[CH:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH2:23][C:22]2[CH:25]=[CH:26][C:27]([Cl:28])=[C:20]([Cl:19])[CH:21]=2)[C:6]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:4]

Participants

5

Reactant 3

HCID 76093,4-Dichlorobenzyl chlorideHCID 24758Sodium hydrideHCID 5107764ethyl 3-formyl-1H-indole-2-carboxylate

Product 1

HCID 22603427Ethyl 3-formyl-N-(3,4-dichlorobenzyl)indole-2-carboxylateYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (488 mg, 60% in mineral oil) was added to a stirred solution of ethyl 3-formylindole-2-carboxylate (2.21 g) in DMF (100 ml) under argon, and reaction stirred at ambient temperature for 25 minutes. 3,4-Dichlorobenzyl chloride (1.71 ml) was then added and the reaction stirred overnight. The reaction mixture was concentrated in vacuo and the residue dissolved in ethyl acetate (80 ml) and washed with water (2×80 ml), dried (MgSO4) and concentrated in vacuo to give a crude residue which was purified by column chromatography using ethyl acetate:iso-hexane as eluent (gradient 5/95-100/0), to give the product as a yellow solid (2.17 g, 57%); NMR d (CD3SOCD3) 1.25 (t, 3H), 4.40 (q, 2H), 5.80 (s, 2H), 7.00 (m, 1H), 7.30-7.50 (m, 3H), 7.55 (m, 1H), 7.65 (m, 1H), 8.35 (m, 1H), 10.48 (s, 1H); M/z (+) 376.4 (MH+).

Workup

  1. customreaction
  2. stirringthe reaction stirred overnight
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. dissolutionthe residue dissolved in ethyl acetate (80 ml)
  5. washwashed with water (2×80 ml)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customto give a crude residue which
  9. customwas purified by column chromatography

Sources & evidence

ORD record
ord-b0b33f07078e4f5a94fc9e0bb5194042
Source dataset
uspto-grants-2004_12
Patent number
US06833387B1

Reaction notes

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