e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Preparative Scale Synthesis of the Biaryl Core of Anacetrapib via a Ruthenium-Catalyzed Direct Arylation Reaction: Unexpected Effect of Solvent Impurity on the …

…, R Angelaud, JF Marcoux, PD O'Shea…

Index: Ouellet, Stephane G.; Roy, Amelie; Molinaro, Carmela; Angelaud, Remy; Marcoux, Jean-Francois; OShea, Paul D.; Davies, Ian W. Journal of Organic Chemistry, 2011 , vol. 76, # 5 p. 1436 - 1439

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Citation Number: 43

Abstract

In this report, we disclose our findings regarding the remarkable effect of a low-level impurity found in the solvent used for a ruthenium-catalyzed direct arylation reaction. This discovery allowed for the development of a robust and high-yield arylation protocol that was demonstrated on a multikilogram scale using carboxylate as the cocatalyst. Finally, a practical, scalable, and chromatography-free synthesis of the biaryl core of Anacetrapib is ...

N/A Structure

~%

4'-Fluoro-2'-methoxy-5'-isopropyl-4-trifluoromethyl-1,1'-biphenyl-2- methanol Structure

4'-Fluoro-2'-me...

1-Bromo-4-fluoro-5-isopropyl-2-methoxybenzene Structure

1-Bromo-4-fluor...

~%

4'-Fluoro-2'-methoxy-5'-isopropyl-4-trifluoromethyl-1,1'-biphenyl-2- methanol Structure

4'-Fluoro-2'-me...

1-(5-Bromo-2-fluoro-4-methoxyphenyl)ethanone Structure

1-(5-Bromo-2-fl...

~%

4'-Fluoro-2'-methoxy-5'-isopropyl-4-trifluoromethyl-1,1'-biphenyl-2- methanol Structure

4'-Fluoro-2'-me...

Benzenemethanol, 5-bromo-2-fluoro-4-methoxy-α,α-dimethyl- Structure

Benzenemethanol...

~%

4'-Fluoro-2'-methoxy-5'-isopropyl-4-trifluoromethyl-1,1'-biphenyl-2- methanol Structure

4'-Fluoro-2'-me...

1-Bromo-2,4-difluorobenzene Structure

1-Bromo-2,4-dif...

~%

4'-Fluoro-2'-methoxy-5'-isopropyl-4-trifluoromethyl-1,1'-biphenyl-2- methanol Structure

4'-Fluoro-2'-me...

2-Bromo-5-fluoroanisole Structure

2-Bromo-5-fluor...

~%

4'-Fluoro-2'-methoxy-5'-isopropyl-4-trifluoromethyl-1,1'-biphenyl-2- methanol Structure

4'-Fluoro-2'-me...

Oxazole, 4,5-dihydro-2-[3-(trifluoromethyl)phenyl]- Structure

Oxazole, 4,5-di...

~%

4'-Fluoro-2'-methoxy-5'-isopropyl-4-trifluoromethyl-1,1'-biphenyl-2- methanol Structure

4'-Fluoro-2'-me...

3-(Trifluoromethyl)benzonitrile Structure

3-(Trifluoromet...

~%

4'-Fluoro-2'-methoxy-5'-isopropyl-4-trifluoromethyl-1,1'-biphenyl-2- methanol Structure

4'-Fluoro-2'-me...

1-(5-Bromo-2-fluoro-4-methoxyphenyl)ethanone Structure

1-(5-Bromo-2-fl...

~%

1-Bromo-4-fluoro-5-isopropyl-2-methoxybenzene Structure

1-Bromo-4-fluor...

1-Bromo-2,4-difluorobenzene Structure

1-Bromo-2,4-dif...

~%

1-Bromo-4-fluoro-5-isopropyl-2-methoxybenzene Structure

1-Bromo-4-fluor...

2-Bromo-5-fluoroanisole Structure

2-Bromo-5-fluor...

~%

1-Bromo-4-fluoro-5-isopropyl-2-methoxybenzene Structure

1-Bromo-4-fluor...

1-Bromo-2,4-difluorobenzene Structure

1-Bromo-2,4-dif...

~%

1-(5-Bromo-2-fluoro-4-methoxyphenyl)ethanone Structure

1-(5-Bromo-2-fl...

Biphenyl-substituted oxazolidinones as cholesteryl ester tra...

[Smith, Cameron J.; Ali, Amjad; Hammond, Milton L.; Li, Hong; Lu, Zhijian; Napolitano, Joann; Taylor, Gayle E.; Thompson, Christopher F.; Anderson, Matt S.; Chen, Ying; Eveland, Suzanne S.; Guo, Qiu; Hyland, Sheryl A.; Milot, Denise P.; Sparrow, Carl P.; Wright, Samuel D.; Cumiskey, Anne-Marie; Latham, Melanie; Peterson, Laurence B.; Rosa, Ray; Pivnichny, James V.; Tong, Xinchun; Xu, Suoyu S.; Sinclair, Peter J. Journal of Medicinal Chemistry, 2011 , vol. 54, # 13 p. 4880 - 4895]

Biphenyl-substituted oxazolidinones as cholesteryl ester tra...

[Smith, Cameron J.; Ali, Amjad; Hammond, Milton L.; Li, Hong; Lu, Zhijian; Napolitano, Joann; Taylor, Gayle E.; Thompson, Christopher F.; Anderson, Matt S.; Chen, Ying; Eveland, Suzanne S.; Guo, Qiu; Hyland, Sheryl A.; Milot, Denise P.; Sparrow, Carl P.; Wright, Samuel D.; Cumiskey, Anne-Marie; Latham, Melanie; Peterson, Laurence B.; Rosa, Ray; Pivnichny, James V.; Tong, Xinchun; Xu, Suoyu S.; Sinclair, Peter J. Journal of Medicinal Chemistry, 2011 , vol. 54, # 13 p. 4880 - 4895]

Biphenyl-substituted oxazolidinones as cholesteryl ester tra...

[Smith, Cameron J.; Ali, Amjad; Hammond, Milton L.; Li, Hong; Lu, Zhijian; Napolitano, Joann; Taylor, Gayle E.; Thompson, Christopher F.; Anderson, Matt S.; Chen, Ying; Eveland, Suzanne S.; Guo, Qiu; Hyland, Sheryl A.; Milot, Denise P.; Sparrow, Carl P.; Wright, Samuel D.; Cumiskey, Anne-Marie; Latham, Melanie; Peterson, Laurence B.; Rosa, Ray; Pivnichny, James V.; Tong, Xinchun; Xu, Suoyu S.; Sinclair, Peter J. Journal of Medicinal Chemistry, 2011 , vol. 54, # 13 p. 4880 - 4895]

Biphenyl-substituted oxazolidinones as cholesteryl ester tra...

[Smith, Cameron J.; Ali, Amjad; Hammond, Milton L.; Li, Hong; Lu, Zhijian; Napolitano, Joann; Taylor, Gayle E.; Thompson, Christopher F.; Anderson, Matt S.; Chen, Ying; Eveland, Suzanne S.; Guo, Qiu; Hyland, Sheryl A.; Milot, Denise P.; Sparrow, Carl P.; Wright, Samuel D.; Cumiskey, Anne-Marie; Latham, Melanie; Peterson, Laurence B.; Rosa, Ray; Pivnichny, James V.; Tong, Xinchun; Xu, Suoyu S.; Sinclair, Peter J. Journal of Medicinal Chemistry, 2011 , vol. 54, # 13 p. 4880 - 4895]