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CAS RN: | Product Number: R0275

Reagents for Suzuki-Miyaura Cross-Coupling Reactions [Pd(dppf)Cl2·CH2Cl2, Cs2CO3] (HPMC encapsulated)


Purity:
Synonyms:
  • Pd(dppf)Cl2·CH2Cl2 ca. 0.03 mmol/capsule, Cs2CO3 ca. 0.7 mmol/capsule (HPMC encapsulated)
Documents:
10EACH
$111.00
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Note:

Contents (per one capsule)

  • Pd(dppf)Cl2·CH2Cl2 : ca. 0.03 mmol
  • Cs2CO3 : ca. 0.7 mmol

Directions for Use

  • Each capsule contains all reagents for a single use on 0.60 mmol scale Suzuki-Miyaura Cross-Coupling Reactions. Typical condition: 0.60 mmol of aryl halide and 1.5 equiv of boronic acid in THF/water (4:1) (0.30 M) at 100 °C.
    (Reference: J. Org. Chem. 2021, 86, 1357.)

Related Products

  • B2064 [1,1'-Bis(diphenylphosphino)ferrocene]palladium(II) Dichloride Dichloromethane Adduct (= Pd(dppf)Cl2·CH2Cl2)
  • C2160 Cesium Carbonate (= Cs2CO3)

Product Number R0275
Physical State (20 deg.C) Solid
Storage Temperature 0-10°C
Store Under Inert Gas Store under inert gas
Condition to Avoid Air Sensitive
Specifications
Appearance White to Light yellow to Light orange capsule
Functionality test (conversion ratio) min. 90.0 %
Properties (reference)
GHS
Pictogram Pictogram Pictogram
Signal Word Danger
Hazard Statements H318 : Causes serious eye damage.
H361 : Suspected of damaging fertility or the unborn child.
H373 : May cause damage to organs through prolonged or repeated exposure.
Precautionary Statements P501 : Dispose of contents/ container to an approved waste disposal plant.
P260 : Do not breathe dust/ fume/ gas/ mist/ vapors/ spray.
P202 : Do not handle until all safety precautions have been read and understood.
P201 : Obtain special instructions before use.
P280 : Wear protective gloves/ protective clothing/ eye protection/ face protection.
P308 + P313 : IF exposed or concerned: Get medical advice/ attention.
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.
P405 : Store locked up.
Related Laws:
Transport Information:
HS Number 3822.19.0080
Application
TCI Practical Example: Suzuki-Miyaura Coupling Using the Capsule Reagent

Suzuki-Miyaura Coupling Using the Capsule Reagent

Used Chemicals

Procedure

Reagents for Suzuki-Miyaura Cross-Coupling Reactions (one capsule) was added to a solution of 2-acetamido-5-bromo-4-methylpyridine (137 mg, 0.60 mmol) and phenylboronic acid (110 mg, 0.90 mmol, 1.5 eq.) in THF/H2O (4:1, 2 mL) at r.t. and the reaction mixture was stirred at 100 °C for 2 hours. The solution was then filtered through Celite pad and the filtrate was diluted with sat. Na2SO4 aq. (15 mL). The aqueous layer was extracted with ethyl acetate (15 mL x 2) and the organic layer was washed with water (15 mL) and brine (15 mL), dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by silica gel chromatography (ethyl acetate:hexane = 2:1 - 1:4) and then further purified by reversed-phase silica gel chromatography (water:acetonitrile = 95:5 - 40:60) to afford 2-acetamido-4-methyl-5-phenylpyridine (122 mg, 90% yield) as a white solid.

Experimenter’s Comments

The reaction mixture was monitored by GC.
The shape of the capsule is like below image and Pd(dppf)Cl2·CH2Cl2 (ca. 0.03 mmol) and Cs2CO3 (ca. 0.7 mmol) are encapsulated in each capsule.
The material of the capsule is water-soluble HPMC (hydroxypropyl methylcellulose).
Since it was difficult to remove the starting material by the normal phase silica gel column purification, so the reverse-phase column purification was performed.

カプセル

Analytical Data

2-Acetamido-4-methyl-5-phenylpyridine

1H NMR (400 MHz, CDCl3); δ 9.24-9.06 (brs, 1H), 8.16 (s, 1H), 8.10 (s, 1H), 7.46-7.36 (m, 3H), 7.30-7.29 (m, 2H), 2.32 (s, 3H), 2.21 (s, 3H).

Lead Reference

Other Reference


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