Sodium Iodide → 3-Chloro-5-iodo-1-(4-isopropoxyphenyl)indole-2-carboxylic acid ethyl ester
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]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
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
- customprepared in accordance with the procedure
- temperatureThe mixture was cooled to room temperature
- washThe combined organic phase was washed with diluted NH4OH solution (2×200 mL), HCl (0.1 N solution; 2×200 mL), brine (100 mL)
- dry with materialdried over Na2SO4
- filtrationFiltration and concentration of the organic phase
Sources & evidence
- ORD record
- ord-6b482356963042a8bfe69931bdc07ee5
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07705023B2
Reaction notes
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