Functionalisation of 2-Methoxy-6-methylpyridine

Gray, Michael A.; Konopski, Leszek; Langlois, Y.

doi:10.1080/00397919408011740

Cited by 24 publications

(9 citation statements)

References 7 publications

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“…[7] Subsequently, methyl 6-(hydroxymethyl) picolinate was bromized by PBr 3 in CHCl 3 and resulted in the smooth conversion to the methyl 6-(bromomethyl)picolinate. [8] The mononuclear cobalt complex 1 was obtained as green solid by treatment of CoCl 2 •6H 2 O with TPA COOMe in refluxed CH 3 CN overnight with a yield of 50.7%. [8] The mononuclear cobalt complex 1 was obtained as green solid by treatment of CoCl 2 •6H 2 O with TPA COOMe in refluxed CH 3 CN overnight with a yield of 50.7%.…”

Section: Resultsmentioning

confidence: 99%

Functional Polypyridine Co Complex as an Efficient Catalyst for Photo‐Induced Water Oxidation

et al. 2016

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A novel mononuclear cobalt complex 1 was synthesized by treatment of CoCl 2 •6H 2 O with a COOMe functionalized TPA ligand (TPA＝tris(2-pyridylmethyl)amine). In a basic borate buffer, 1 acts as an efficient catalyst for water oxidation, which is confirmed by an extinct catalytic oxidant wave in electrochemistry. Visible light-driven water oxidation has been achieved by 1 with a TON of 127.7 and a TOF of 3.8 s 1 respectively in a homogeneous system. In comparison to the reference RC with naked TPA, the higher efficiency of 1 evidences COOMe on ligand can improve the catalytic efficiency, leading to an effective pathway towards construction of a robust and stable artificial photosynthesis system.

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Section: Resultsmentioning

confidence: 99%

Functional Polypyridine Co Complex as an Efficient Catalyst for Photo‐Induced Water Oxidation

et al. 2016

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“…Our first attempt to label the 2‐methoxy‐6‐methylpyridine boronate adapted a procedure described by Gray et al , in which 2‐hydroxy‐6‐methylpyridine, silver carbonate, and iodomethane were stirred in chloroform protected from light for 40 h . Unfortunately, this method did not work when using an analog substrate, 6‐(4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolan‐2‐yl)pyridine‐2‐ol (Scheme , right side).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of isotope‐labeled HSP90 inhibitor: [¹³CD₃] and [¹⁴C]‐TAK‐459

Plesescu

Elliott

et al. 2014

Labelled Comp Radiopharmac

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[(13) CD3 ]-TAK-459 (1A), an HSP90 inhibitor, was synthesized from [(13) CD3 ]-sodium methoxide in three steps in an overall yield of 29%. The key intermediate [(13) CD3 ]-2-methoxy-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine was synthesized in two steps from 2,6-dibromopyridine and stable isotope-labeled sodium methoxide. [(14) C]-TAK-459 (1B) was synthesized from [(14) C(U)]-guanidine hydrochloride in five steps in an overall radiochemical yield of 5.4%. The key intermediate, [(14) C]-(R)-2-amino-7-(2-bromo-4-fluorophenyl)-4-methyl-7,8-dihydropyrido[4,3-d]pyrimidin-5(6H)-one, was prepared by microwave-assisted condensation.

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“…The synthetic strategy employed by Discovery Chemistry for the preparation of clinical candidate 2 is outlined in Scheme . − A key feature to the synthesis involved a Pd-mediated coupling of 6-methoxy-3-bromo-2-methyl pyridine 3 with 4-iodo-4-methylisoxazole 5 , followed by isomerization under basic conditions to provide β-ketonitrile 7 as the sodium enolate form . Treatment of 7 with excess hydrazine monohydrate in refluxing toluene afforded aminopyrazole 8 in 76% yield over the two steps from oxazole 6 .…”

Section: Introductionmentioning

confidence: 99%

The Development of a Robust Process for a CRF₁ Receptor Antagonist

Broxer

Fitzgerald

Sfouggatakis

et al. 2011

Org. Process Res. Dev.

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A scalable and robust process was developed for the preparation of pexacerfont (2), a pyrazolotriazine corticotropin-releasing factor receptor 1 antagonist (CRF1). The formation of the core hydroxypyrazolotriazine moiety was achieved through two consecutive cyclizations of a semicarbazide, employing reaction conditions that are significantly milder than those reported in the literature. Further conversion to the key chloropyrazolotriazine intermediate was accomplished through a novel catalytic process using phosphorous oxychloride as the chlorinating agent. The active pharmaceutical ingredient 2 was obtained in >99.5% purity with a 68% overall yield for the six synthetic steps.

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Functionalisation of 2-Methoxy-6-methylpyridine

Cited by 24 publications

References 7 publications

Functional Polypyridine Co Complex as an Efficient Catalyst for Photo‐Induced Water Oxidation

Functional Polypyridine Co Complex as an Efficient Catalyst for Photo‐Induced Water Oxidation

Synthesis of isotope‐labeled HSP90 inhibitor: [¹³CD₃] and [¹⁴C]‐TAK‐459

The Development of a Robust Process for a CRF₁ Receptor Antagonist

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Functionalisation of 2-Methoxy-6-methylpyridine

Cited by 24 publications

References 7 publications

Functional Polypyridine Co Complex as an Efficient Catalyst for Photo‐Induced Water Oxidation

Functional Polypyridine Co Complex as an Efficient Catalyst for Photo‐Induced Water Oxidation

Synthesis of isotope‐labeled HSP90 inhibitor: [13CD3] and [14C]‐TAK‐459

The Development of a Robust Process for a CRF1 Receptor Antagonist

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Synthesis of isotope‐labeled HSP90 inhibitor: [¹³CD₃] and [¹⁴C]‐TAK‐459

The Development of a Robust Process for a CRF₁ Receptor Antagonist