5-cyano-1-methyl-1H-pyrrol-2-ylboronic acid synthesis

3synthesis methods

Product Name:5-cyano-1-methyl-1H-pyrrol-2-ylboronic acid
CAS Number:860617-71-6
Molecular formula:C6H7BN2O2
Molecular Weight:149.94

34884-10-1 Synthesis

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5-cyano-1-methyl-1H-pyrrol-2-ylboronic acid

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Yield: 70%

Reaction Conditions:

Stage #1:1-methyl-1H-pyrrole-2-carbonitrile with Triisopropyl borate;lithium diisopropyl amide in tetrahydrofuran at -4 - 13; for 2 h;
Stage #2: with hydrogenchloride;water in tetrahydrofuran

Steps:

1.C
The solution of 1-methylpyrrole-2-carbonitrile (0.131 g, 1.23 mmol), triisopropylborate (250 µL, 1.08 mmol), and THF (4 mL) was cooled to about -4 °C and 2M LDA (0.6 mL, 1.2 mmol) was added dropwise from a syringe. The bath was removed and the suspension was allowed to warm to about 13 °C within about 2 hours. After cooling and quenching with water and 5% aqueous HCI, the product was extracted with diethylether. The organic layer was evaporated to give an oil which solidified upon standing to give 0.130 g (70% yield) of (5-cyano-1-methyl-1H-pyrrol- 2-yl) boronic acid. ¹H-NMR (DMSO-d6) : No. 8.38, 6.87, 6.77, and 3.88.

References:

WYETH WO2005/105817, 2005, A2 Location in patent:Page/Page column 24

Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-

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References

96-54-8 Synthesis

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References