3,4-Dichlorobenzyl chloride → Methyl N-(3,4-dichlorobenzyl)-2-methoxycarbonyl-3-indoleacetate

HRID 2307916Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

3,4-Dichlorobenzyl chloride (8.2 g) was added to a stirred solution of methyl 2-methoxycarbonyl-3-indoleacetate (6.5 g) and potassium carbonate (8.36 g) in acetonitrile (200 ml) under an atmosphere of argon. The reaction was heated to 80° C. for 24 hours. The reaction was concentrated in vacuo and partitioned between ethyl acetate and water. Combined organic extracts were washed with saturated aqueous sodium chloride solution, dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography using 25% ethyl acetate:iso-hexane as eluent to give the product as a white solid (6.95 g, 65%), NMR d (CD3SOCD3) 3.60 (s, 3H), 3.77 (s, 3H), 4.13 (s, 2H), 5.89 (s, 2H), 6.89 (dd, 1H), 7.16 (t, 1H), 7.27 (d, 1H), 7.34 (t, 1H), 7.52 (d, 1H), 7.57 (d, 1H), 7.78 (d, 1H); M/z (+) 406 (MH+).

Workup

concentrationThe reaction was concentrated in vacuo
custompartitioned between ethyl acetate and water
washCombined organic extracts were washed with saturated aqueous sodium chloride solution
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography

Sources & evidence

ORD record: ord-3cf926484c394417b443da5113a6b4e4
Source dataset: uspto-grants-2004_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06833387B1

Reaction notes

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