Sodium Iodide → HCID 21938261, compound

HRID 2187757Notes

Reaction equation

HRID 2187757 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

8

Reactant 5

HCID 5238Sodium IodideHCID 14798Sodium HydroxideHCID 444305L-Tartaric acidHCID 12230324HCID 12230324, compoundHCID 2193833292059-86-4

Product 1

HCID 21938261HCID 21938261, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

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=1/4 to 1/2), 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

  1. extractionThe reaction mixture is extracted with water and ethyl acetate
  2. additionadded
  3. washthe organic layer is washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe resulting residue is purified through silica gel column chromatography (eluent: ethyl acetate/hexane=1/4 to 1/2)
  7. customcrystallized from a mixed solution of hexane and ethyl acetate

Sources & evidence

ORD record
ord-b8e0c3b709f34f3d95003571900fc85a
Source dataset
uspto-grants-2002_06
Patent number
US06410584B1

Reaction notes

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