IRIS publication 67960169
Process Development and Pilot-Plant Synthesis of (2-Chlorophenyl)[2-(phenylsulfonyl)pyridin-3-yl]methanone
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TY - JOUR - Kopach, Michael E; Kobierski, Michael E; Coffey, D. Scott; Alt, Charles A; Zhang, Tony; Borghese, Alfio; Trankle, William G; Roberts, Dilwyn J; Moynihan, Humphrey; Lorenz, Kurt; McNamara, Oria A; Kissane, Marie; Maguire, Anita R - 2010 - Unknown - Organic Process Research ; Development - Process Development and Pilot-Plant Synthesis of (2-Chlorophenyl)[2-(phenylsulfonyl)pyridin-3-yl]methanone - Validated - WOS: 6 () - 14 - 5 - 1229 - 1238 - Routes to (2-chlorophenyl)[2-(phenylsulfonyl)pyridin-3-yl]methanone, 1, an intermediate in the manufacture of NK1-II inhibitor LY686017 are described which produce 1 in > 75\% yield and 95\% purity. A highly selective telescoped ortho lithation/condensation/oxidation process was developed and successfully scaled to the clinical pilot plant to produce 25 kg of 1. For the pilot-plant campaign, the lithiation step was developed to operate at -50 degrees C using commercial lithium diisopropylamide (LOA), and the oxidation step employed catalytic TEMPO as the primary and NaOCI as the terminal oxidant. After completion of the pilot-plant campaign second-generation approaches to 1 were developed to improve process greenness where the lithiation and condensation step were operated as warm as -10 degrees C, the highly efficient AZADO catalyst was used as a substitute for TEMPO in the Anelli-Montanari oxidation, and process mass intensity was reduced 25\%. - 10.1021/op100157q DA - 2010/NaN ER -
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@article{V67960169, = {Kopach, Michael E and Kobierski, Michael E and Coffey, D. Scott and Alt, Charles A and Zhang, Tony and Borghese, Alfio and Trankle, William G and Roberts, Dilwyn J and Moynihan, Humphrey and Lorenz, Kurt and McNamara, Oria A and Kissane, Marie and Maguire, Anita R}, = {2010}, = {Unknown}, = {Organic Process Research ; Development}, = {Process Development and Pilot-Plant Synthesis of (2-Chlorophenyl)[2-(phenylsulfonyl)pyridin-3-yl]methanone}, = {Validated}, = {WOS: 6 ()}, = {14}, = {5}, pages = {1229--1238}, = {{Routes to (2-chlorophenyl)[2-(phenylsulfonyl)pyridin-3-yl]methanone, 1, an intermediate in the manufacture of NK1-II inhibitor LY686017 are described which produce 1 in > 75\% yield and 95\% purity. A highly selective telescoped ortho lithation/condensation/oxidation process was developed and successfully scaled to the clinical pilot plant to produce 25 kg of 1. For the pilot-plant campaign, the lithiation step was developed to operate at -50 degrees C using commercial lithium diisopropylamide (LOA), and the oxidation step employed catalytic TEMPO as the primary and NaOCI as the terminal oxidant. After completion of the pilot-plant campaign second-generation approaches to 1 were developed to improve process greenness where the lithiation and condensation step were operated as warm as -10 degrees C, the highly efficient AZADO catalyst was used as a substitute for TEMPO in the Anelli-Montanari oxidation, and process mass intensity was reduced 25\%.}}, = {10.1021/op100157q}, source = {IRIS} }
Data as stored in IRIS
AUTHORS | Kopach, Michael E; Kobierski, Michael E; Coffey, D. Scott; Alt, Charles A; Zhang, Tony; Borghese, Alfio; Trankle, William G; Roberts, Dilwyn J; Moynihan, Humphrey; Lorenz, Kurt; McNamara, Oria A; Kissane, Marie; Maguire, Anita R | ||
YEAR | 2010 | ||
MONTH | Unknown | ||
JOURNAL_CODE | Organic Process Research ; Development | ||
TITLE | Process Development and Pilot-Plant Synthesis of (2-Chlorophenyl)[2-(phenylsulfonyl)pyridin-3-yl]methanone | ||
STATUS | Validated | ||
TIMES_CITED | WOS: 6 () | ||
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VOLUME | 14 | ||
ISSUE | 5 | ||
START_PAGE | 1229 | ||
END_PAGE | 1238 | ||
ABSTRACT | Routes to (2-chlorophenyl)[2-(phenylsulfonyl)pyridin-3-yl]methanone, 1, an intermediate in the manufacture of NK1-II inhibitor LY686017 are described which produce 1 in > 75\% yield and 95\% purity. A highly selective telescoped ortho lithation/condensation/oxidation process was developed and successfully scaled to the clinical pilot plant to produce 25 kg of 1. For the pilot-plant campaign, the lithiation step was developed to operate at -50 degrees C using commercial lithium diisopropylamide (LOA), and the oxidation step employed catalytic TEMPO as the primary and NaOCI as the terminal oxidant. After completion of the pilot-plant campaign second-generation approaches to 1 were developed to improve process greenness where the lithiation and condensation step were operated as warm as -10 degrees C, the highly efficient AZADO catalyst was used as a substitute for TEMPO in the Anelli-Montanari oxidation, and process mass intensity was reduced 25\%. | ||
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DOI_LINK | 10.1021/op100157q | ||
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