ChemicalBook CAS DataBase List 6-Methylpyridine-3-boronic Acid

6-Methylpyridine-3-boronic Acid synthesis

4synthesis methods

Product Name:6-Methylpyridine-3-boronic Acid
CAS Number:659742-21-9
Molecular formula:C6H8BNO2
Molecular Weight:136.94

2-METHYL-5-PYRIDINETRIFLUOROMETHANESULF&

111770-91-3

73183-34-3

659742-21-9

General procedure for the synthesis of 6-methyl-3-pyridineboronic acid from 6-methyl-3-pyridinol trifluoromethanesulfonate and bis(pinacolato)diboronate: 6-methyl-3-pyridinol trifluoromethanesulfonate (4.6 mmol) was dissolved in acetonitrile (30 mL) and transferred to a 5 mL microwave reaction tube. To this solution was added 1.5 equivalents of bis(pinacolato)diboron (6.9 mmol; 1.71 g). The mixture was stirred on a magnetic stirrer until complete dissolution. Subsequently, potassium acetate (13.8 mmol; 1.35 g) and [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (98 mg, 0.03 mol%) were added to the mixture. The reaction mixture was placed in a microwave reactor and heated at 160°C for 2 x 600 seconds. Upon completion of the reaction (monitored by LC-MS), the acetonitrile was removed by evaporation to give a black solid. The solid was dissolved in DMSO and purified by HPLC to give the final target product 6-methyl-3-pyridineboronic acid (580 mg, 92% yield; 4.2 mmol). Mass spectral data: MH+ = 138.

111770-91-3
27 suppliers
$41.29/1g

73183-34-3
589 suppliers
$6.00/5g

659742-21-9
226 suppliers
$12.00/250mg

Yield:659742-21-9 92%

Reaction Conditions:

with potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride in acetonitrile at 160; for 0.333333 h;Microwave;

Steps:

1b
The INFLATE (4. 6MMOL) was dissolved in acetonitrile (30MOL) and placed into A 5M . microwave vessel. To the solution was added 1. 5 EQ of bis (PINACOLATO) DIBORON (6. 9MMOL ; 1. 71 G). The mixture was stirred on A magnetic stir plate until dissolution. To the mixture was added KOAC (13. 8MMOL ; 1. 35g) and 98mg of [1,1'-bis (DIPHENYLPHOSPHINO)- FERROCENE] DICHLOROPALLADIUM (II) (0. 03MOI%). The reaction mixture was heated at 160°C for 2 X 600s. After completion (monitored by LC-MS), the acetonitrile was evaporated to give a black solid. The solid was dissolved in DMSO, ms and purified by HPLC to give the boronic acid (580mg, 92%; 4. 2MMOL). MS: MH+= 138

References:

RENOVIS, INC. WO2005/32493, 2005, A2 Location in patent:Page/Page column 40-41

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3430-13-5 Synthesis