Development of a Green and Sustainable Manufacturing Process for a Key Intermediate to Nemtabrutinib (MK-1026): Sequential Deprotonation–Lithiation as a Batch

Development of a Green and Sustainable Manufacturing Process for a Key Intermediate to Nemtabrutinib (MK-1026): Sequential Deprotonation–Lithiation as a Batch–Flow Process

Published:2024-05-09 Issue:5 Volume:28 Page:1402-1410
ISSN:1083-6160
Container-title:Organic Process Research & Development
language:en
Short-container-title:Org. Process Res. Dev.

Author:

Otte Douglas A. L.¹,Larson Reed T.¹,Alwedi Embarek¹^ORCID,Armiger Travis¹^ORCID,Chen Yonggang¹,Chung Cheol K.¹^ORCID,Corry James¹,Desmond Richard¹,Fier Patrick S.¹^ORCID,Franklin Robert D.¹^ORCID,Guetschow Erik D.²,Hall Jackson R.²,Halsey Holst M.¹,Hartmanshenn Clara¹,Jellett Lisa³,Kuhl Nadine¹^ORCID,Lévesque François¹,McMullen Jonathan P.¹^ORCID,Patel Pratiq A.³,Paulines Mellie June²,Ren Hong¹^ORCID,Rodrigues Vailankanni L.¹,Ruccolo Serge¹,Tan Lushi¹,Thaisrivongs David A.¹^ORCID,Xiao Kai-Jiong¹^ORCID

Affiliation:

1. Department of Process Research and Development, Merck & Co., Inc., Rahway, New Jersey 07065, United States

2. Department of Analytical Research and Development, Merck & Co., Inc., Rahway, New Jersey 07065, United States

3. Global Pharmaceutical Commercialization Development, Merck & Co., Inc., Rahway, New Jersey 07065, United States

Publisher

American Chemical Society (ACS)

Link

https://pubs.acs.org/doi/pdf/10.1021/acs.oprd.3c00510

Reference12 articles.

1. Role of Bruton’s tyrosine kinase in B cells and malignancies

2. Utilizing biocatalysis and a sulfolane-mediated reductive acetal opening to access nemtabrutinib from cyrene

3. Highly Functionalized Organomagnesium Reagents Prepared through Halogen-Metal Exchange

4. Some Factors Affecting Halogen-Metal Interconversions

5. USE OF METHYLLITHIUM IN METAL/HALOGEN EXCHANGE; A MILD AND EFFICIENT METHOD FOR THE SYNTHESIS OFORTHOSUBSTITUTED TOLUENES

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1. Pilot-Scale Operation and Characterization of an Organolithium-Mediated Coupling Reaction in Flow to Form a Ketone Intermediate on the Route to Nemtabrutinib;Organic Process Research & Development;2024-05-09