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Sodium Iodide → 3-Chloro-5-iodo-1-(4-isopropoxyphenyl)indole-2-carboxylic acid ethyl ester

HRID 646137
Notes
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Reaction equation

HRID 646137 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH:24]([CH3:26])[CH3:25])=[CH:19][CH:18]=2)[C:8]2[C:13]([C:14]=1[Cl:15])=[CH:12][C:11](Br)=[CH:10][CH:9]=2)=[O:5])[CH3:2].[Na+].[I-:28].CNCCNC.O1CCOCC1>CCOC(C)=O.[Cu]I>[CH2:1]([O:3][C:4]([C:6]1[N:7]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH:24]([CH3:26])[CH3:25])=[CH:19][CH:18]=2)[C:8]2[C:13]([C:14]=1[Cl:15])=[CH:12][C:11]([I:28])=[CH:10][CH:9]=2)=[O:5])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 8070N,N'-DimethylethylenediamineHCID 312751,4-DioxaneHCID 686966545-Bromo-3-chloro-1-(4-isopropoxyphenyl)indole-2-carboxylic acid ethyl ester

Product 1

HCID 686997713-Chloro-5-iodo-1-(4-isopropoxyphenyl)indole-2-carboxylic acid ethyl esterYield 97%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 5-bromo-3-chloro-1-(4-isopropoxyphenyl)-1H-indole-2-carboxylic acid ethyl ester (2.80 g, 6.44 mmol) (prepared in accordance with the procedure described in Example 35, Method 1, step (b)), CuI (122 mg, 0.64 mmol), NaI (1.94 g, 12.9 mmol), N,N′-dimethyl-1,2-diaminoethane (142 μL, 1.28 mmol) and 1,4-dioxane (10 ml) was stirred at 120° C. for 24 h. The mixture was cooled to room temperature and diluted with EtOAc (200 ml). The combined organic phase was washed with diluted NH4OH solution (2×200 mL), HCl (0.1 N solution; 2×200 mL), brine (100 mL) and dried over Na2SO4. Filtration and concentration of the organic phase gave the sub-title compound (3.02 g 97%).

Workup

  1. customprepared in accordance with the procedure
  2. temperatureThe mixture was cooled to room temperature
  3. washThe combined organic phase was washed with diluted NH4OH solution (2×200 mL), HCl (0.1 N solution; 2×200 mL), brine (100 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationFiltration and concentration of the organic phase

Sources & evidence

ORD record
ord-6b482356963042a8bfe69931bdc07ee5
Source dataset
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07705023B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes