Sodium Iodide → HCID 21938261, compound

HRID 1242147Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([CH3:14])=[CH:8]2)=[O:4].[Cl:15][C:16]1[CH:23]=[C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:21]=[CH:20][C:17]=1[CH2:18]Br.C(O)(=O)[C@@H]([C@H](C(O)=O)O)O.[OH-].[Na+].[I-].[Na+]>O.O1CCOCC1>[Cl:15][C:16]1[CH:23]=[C:22]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:21]=[CH:20][C:17]=1[CH2:18][C:8]1[C:7]2[C:11](=[CH:12][CH:13]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:6]=2)[NH:10][C:9]=1[CH3:14]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 5-methoxycarbonyl-2-methylindole (0.84 g), 2-chloro-4-phenylbenzyl bromide (2.0 g), L-tartaric acid (1.07 g), sodium hydroxide (0.37 g), sodium iodide (0.53 g), 1,4-dioxane (15 ml) and water (8 ml) is stirred at 90° C. for 4 hours. The reaction mixture is extracted with water and ethyl acetate added thereto, and the organic layer is washed with water, dried and concentrated. The resulting residue is purified through silica gel column chromatography (eluent: ethyl acetate/hexane=¼ to ½), and crystallized from a mixed solution of hexane and ethyl acetate to obtain 3-(2-chloro-4-phenylbenzyl)-5-methoxycarbonyl-2-methylindole (144) (0.965).

Workup

extractionThe reaction mixture is extracted with water and ethyl acetate
additionadded
washthe organic layer is washed with water
customdried
concentrationconcentrated
customThe resulting residue is purified through silica gel column chromatography (eluent: ethyl acetate/hexane=¼ to ½)
customcrystallized from a mixed solution of hexane and ethyl acetate

Sources & evidence

ORD record: ord-17dee2af880046bfb139da7c422e3d60
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07115647B2

Reaction notes

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