Specifications
CLASS
Organoboron [Organometallic Reagents]
SUBCLASS
Boronic Acids and Derivatives [Organoboron]
APPLICATION
Introduction of an aminomethyl group by Suzuki-Miyaura cross-coupling reaction
General Procedure for the Suzuki?Miyaura Cross-coupling Reaction: A sealed tube is charged with potassium (tert-butoxycarbonyl)amino)methyl)trifluoroborate (62 mg, 0.263 mmol, 1.05 equiv), an aryl or heteroaryl chloride (0.25 mmol, 1.0 equiv), Pd(OAc)2 (3 mg, 0.013 mmol, 0.05 equiv), SPhos ligand (0.03 mmol, 0.1 equiv) and K2CO3 (104 mg, 0.75 mmol, 3.0 equiv). The mixture is then purged with argon. Toluene/H2O (4:1, 0.8 mL / 0.2 mL) is then added to the reaction tube. The reaction mixture is stirred for 22 h at 85 °C and then cooled to rt. A solution of pH 7 buffer (2 mL) is added, and the resulting mixture is extracted with EtOAc (2 × 3 mL). The organic layer is combined, dried (MgSO4) and filtered. The solvent is removed in vacuo and the product is purified by column chromatography to give the corresponding compound in shown yield.
PUBCHEM SUBSTANCE ID
253661860.0
BEILSTEIN/REAXYS NUMBER
21751374.0
HAZARD STATEMENTS
H315 : Causes skin irritation.
H319 : Causes serious eye irritation.
PRECAUTIONARY STATEMENTS
P264 : Wash skin thoroughly after handling.
P280 : Wear protective gloves/ eye protection/ face protection.
P337 + P313 : If eye irritation persists: Get medical advice/ attention.
P305 + P351 + P338 : IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P302 + P352 : IF ON SKIN: Wash with plenty of soap and water.
P332 + P313 : If skin irritation occurs: Get medical advice/ attention.
P362 : Take off contaminated clothing and wash before reuse.
*USAGE / SAFETY STATEMENT
For laboratory research and development purposes only.
QUALITY CERTIFICATION / COMPLIANCE
Fukaya factory is certified for GMP, ISO14001:2004 (JQA-EM5386) and IQ Net (JP-JQA-EM5386).
APPEARANCE
White to Almost white powder to crystal
MOLECULAR FORMULA
C6H12BF3KNO2
PURITY / ANALYSIS METHOD
>97.0%(N)