Potassium Carbonate → Ethyl 5-acetoxy-N-(3,4-dichlorobenzyl)indole-2-carboxylate

HRID 1166057Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[CH2:5]Br.[C:11]([O:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][C:19]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:18]2)(=[O:13])[CH3:12].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:11]([O:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[N:20]([CH2:5][C:4]1[CH:7]=[CH:8][C:9]([Cl:10])=[C:2]([Cl:1])[CH:3]=1)[C:19]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:18]2)(=[O:13])[CH3:12]

Participants

Conditions

Temperature: 80 °C

Procedure

3,4-Dichlorobenzyl bromide (5.96 g) was added to a stirred solution of ethyl 5-acetoxyindole-2-carboxylate (5.4 g) and potassium carbonate (6.94 g) in acetonitrile (500 ml) under an atmosphere of argon. The reaction was heated at 80° C. for 16 hours, then concentrated in vacuo and the residue partitioned between ethyl acetate and water. Combined organic extracts were washed with water, saturated aqueous sodium chloride and dried (MgSO4). The solvent was removed in vacuo and the residue was triturated with iso-hexane to give the product as a cream solid (5.55 g, 63%): NMR δ(CD3SOCD3) 1.27 (t, 3H), 2.27 (s, 3H), 4.28 (q, 2H), 5.82 (s, 2H), 6.90 (d, 1H), 7.09 (dd, 1H), 7.33-7.40 (m, 2H), 7.46 (d, 1H), 7.52 (d, 1H), 7.60 (d, 1H).

Workup

concentrationconcentrated in vacuo
customthe residue partitioned between ethyl acetate and water
washCombined organic extracts were washed with water, saturated aqueous sodium chloride
dry with materialdried (MgSO4)
customThe solvent was removed in vacuo
customthe residue was triturated with iso-hexane

Sources & evidence

ORD record: ord-36ba3a3c414a4e468bfa62d7175bbef9
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06613760B1

Reaction notes

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