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Supplemental Product Information:
Contents (per one capsule)
2,2'-Bipyridyl ca. 0.500 mmol
Uses of Reagent
Applicable to copper-catalyzed reactions due to a ligand encapsulated in HPMC capsules
H301 + H311 : Toxic if swallowed or in contact with skin. H373 : May cause damage to organs through prolonged or repeated exposure. H341 : Suspected of causing genetic defects.
Precautionary Statements
P260 : Do not breathe dust. P201 : Obtain special instructions before use. P264 : Wash skin thoroughly after handling. P280 : Wear protective gloves/ protective clothing/ eye protection/ face protection/ hearing protection. P301 + P310 + P330 : IF SWALLOWED: Immediately call a POISON CENTER/doctor. Rinse mouth. P302 + P352 + P312 : IF ON SKIN: Wash with plenty of water. Call a POISON CENTER/doctor if you feel unwell.
Copper(I) iodide (HPMC encapsulated) (one capsule) and 2,2’-bipyridyl (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 5 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 organic layer was 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 (71 mg, 46% 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 2,2’-bipyridyl (ca. 500 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.
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