ChemicalBook CAS DataBase List 6-Iodoxindole

6-Iodoxindole synthesis

4synthesis methods

Product Name:6-Iodoxindole
CAS Number:919103-45-0
Molecular formula:C8H6INO
Molecular Weight:259.04

99365-40-9
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$6.00/1g

919103-45-0
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$111.00/100mg

Yield:919103-45-0 84%

Reaction Conditions:

with sodium iodide;copper(l) iodide;trans-N,N'-dimethylcyclohexane-1,2-diamine in 1,4-dioxane at 110; for 24 h;

Steps:

1

Preparation 1: 6-Iodooxindole A schlenk tube and stir bar were dried in an oven overnight and then were evacuated, filled with Ar_(g)and cooled. The schlenk tube was charged with CuI (45 mg, 0.236 mmol, 5 mol %), 6-bromoxindole (1.0 g, 4.72 mmol), and NaI (1.42 g, 9.44 mmol). The schlenk tube was evacuated and backfilled with Ar_(g)(3 times). Racemic trans-N,N'-dimethyl-1,2-cyclohexanediamine (74 μL, 0.472 mmol, 10 mol %) and anhydrous dioxane (4.72 mL) were added via syringe under Ar_(g). The schlenk tube was sealed with a teflon valve and the suspension was stirred at 110° C. for 24 h. The reaction was then cooled to room temperature and 15% NH₄OH_(aq)(50 mL) was added to the reaction mixture while stirring. The suspension was allowed to stir for about 30 min after which the tan solid was vacuum filtered and dried affording 6-Iodooxindole in 84% yield (1.027 g, 3.96 mmol).

References:

US2007/15748,2007,A1 Location in patent:Page/Page column 5

88-73-3 Synthesis