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Supplemental Product Information:
Contents (per one capsule)
CuI ca. 0.800 mmol
Uses of Reagent
Applicable to copper-catalyzed reactions due to a copper catalyst encapsulated in HPMC capsules
H302 : Harmful if swallowed. H315 : Causes skin irritation. H318 : Causes serious eye damage. H373 : May cause damage to organs through prolonged or repeated exposure. H317 : May cause an allergic skin reaction. H335 : May cause respiratory irritation. H410 : Very toxic to aquatic life with long lasting effects.
Precautionary Statements
P273 : Avoid release to the environment. P260 : Do not breathe dust. P264 : Wash skin thoroughly after handling. P280 : Wear protective gloves/ eye protection/ face protection. P391 : Collect spillage. P305 + P351 + P338 + P310 : IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER/doctor.
Copper(I) iodide (HPMC encapsulated) (one capsule) and 8-quinolinol (HPMC encapsulated) (one capsule) were added to a solution of indole (93.7 mg, 800 µmol), 2-bromopyridine (164 mg, 1.04 mmol, 1.3 eq.) and cesium carbonate (521 mg, 1.60 mmol, 2.0 eq.) in DMSO (2.5 mL) at r.t. and the reaction mixture was stirred at 150 °C for 4 hours. After cooling to r.t., the solution was diluted with ethyl acetate (15 mL) and sat. Na2SO4 aq. (15 mL), and filtered through Celite pad. The filtrate was extracted with ethyl acetate (15 mL x 2) and the combined organic layer was washed with 2 mol/L HCl (15 mL) and sat. NaHCO3 aq. (15 mL), dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (ethyl acetate:hexane = 1:10 - 1:5) to afford N-(2-pyridyl)indole (97 mg, 62% yield) as a pale-yellow oil.
Experimenter’s Comments
The reaction mixture was monitored by UPLC. The material of the capsule is water-soluble HPMC (hydroxypropyl methylcellulose). The capsule has the shape shown in Fig. 1 and 8-quinolinol (ca. 450 μmol) and copper(I) iodide (ca. 800 μmol) are encapsulated in each capsule, respectively.
Fig. 1. Appearance of the capsule The capsule dissolves in water or polar solvent as shown in Fig. 2. Fig. 2. Capsule disintegrating (left) Immediately after the addition of the capsule, (right) 15 minutes after the addition of the capsule.
Copper(I) iodide (HPMC encapsulated) (one capsule) and 1,10-phenanthroline (HPMC encapsulated) (one capsule) were added to a solution of indole (93.7 mg, 800 µmol), 2-bromopyridine (164 mg, 1.04 mmol, 1.3 eq.) and cesium carbonate (521 mg, 1.60 mmol, 2.0 eq.) in DMSO (2.5 mL) at r.t. and the reaction mixture was stirred at 150 °C for 2 hours. After cooling to r.t., the solution was diluted with ethyl acetate (15 mL) and sat. Na2SO4 aq. (15 mL), and filtered through Celite pad and the filtrate was extracted with ethyl acetate (15 mL x 2). The organic layer was washed with 2 mol/L HCl (15 mL) and sat. NaHCO3 aq. (15 mL), dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (ethyl acetate:hexane = 10:1 - 5:1) to afford N-(2-pyridyl)indole (130 mg, 84% yield) as a pale-yellow oil.
Experimenter’s Comments
The reaction mixture was monitored by UPLC. The material of the capsule is water-soluble HPMC (hydroxypropyl methylcellulose). The capsule has the shape shown in Figure 1 and 1,10-phenanthroline (ca. 200 μmol) and copper(I) iodide (ca. 800 μmol) are encapsulated in each capsule, respectively.
Figure 1. Appearance of capsule The capsules dissolves in water or polar solvents as shown in Figure 2. Figure 2. Capsule disintegrating (left) Just after the capsule is put in, (right) 15 minutes after the capsule is put in
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