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. 2010 May 21;12(10):2314-7.
doi: 10.1021/ol100671v.

General method for synthesis of 2-heterocyclic N-methyliminodiacetic acid boronates

Graham R Dick  1 , David M Knapp, Eric P Gillis, Martin D Burke
Affiliations

General method for synthesis of 2-heterocyclic N-methyliminodiacetic acid boronates

Graham R Dick et al. Org Lett. .

Abstract

A wide range of 2-pyridyl and other difficult-to-access heterocyclic N-methyliminodiacetic acid boronates can be readily prepared from the corresponding bromides via a new method involving direct transligation of 2-heterocyclic trialkoxyborate salts with N-methyliminodiacetic acid (MIDA) at elevated temperatures.

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Figures

Figure 1
Figure 1
A new method that provides access to a wide range of 2-pyridyl and other difficult-to-access MIDA boronates from the corresponding readily-available bromides.
Figure 2
Figure 2
A. A method for the preparation of 2-pyridyl MIDA boronate 1a from 2a via the intermediacy of triisopropoxyborate salt 3. B. Yield of 1a (via 1H NMR, average of two runs) as a function of the internal reaction temperature.
Scheme 1
Scheme 1
Scheme 2
Scheme 2
Scheme 3
Scheme 3
See this image and copyright information in PMC

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