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PCT Int. Appl. WO2007095588
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PCT Int. Appl. WO2005037793
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F. Rohl, V. Harries, E. Ammermann, G. Lorenz, S. Strathmann, A. Ptock, H. Sauter, W. Gammenos, T. Grote, H. Bayer, R. Kirstgen, K. Oberdorf, B. Muller, and R. Muller, PCT Int. Appl. WO9812179, 1998. Examples of pyrazolylboronic acid derivatives
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PCT Int. Appl. WO2006136830
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PCT. Int., Appl. WO2005012254
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I. Bruce, J. F. Hayler, G. C. Bloomfield, L. Edwards, B. Cox, and C. Howsham, PCT. Int., Appl. WO2007134828, 2007 reports the preparation of 4 and one example of a Suzuki-Miyaura cross-coupling reaction (with 3-bromo-l-methyl-l H -pyrazolo[3,4-d]pyrimidin-6-ylamine). The only analytical data given for 4 was the mass spectrum of its hydrochloride salt
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PCT. Int., Appl. WO2007134828
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Bruce, I.1
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80
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and references therein. Pyrazolylboronic acids and esters are known to be prone to protodeboronation: Ref. 23c and 23e By-products obtained alongside product 52 were the product obtained from homo-coupling of the boronic acid, and debrominated compound 36 (which co-eluted during column chromatography), and unreacted starting material 50 (16%)
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