ethyl 1-{3-[6-(1-hydroxy-1-methylethyl)-1-oxido-pyridin-3-yl]phenyl}-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxylate

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Chemical Name:ethyl 1-{3-[6-(1-hydroxy-1-methylethyl)-1-oxido-pyridin-3-yl]phenyl}-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxylate
CAS No.:694489-61-7
Molecular Formula:C₂₅H₂₃N₃O₅
Molecular Weight:445.475
Hs Code.:

Synonyms:ethyl 1-{3-[6-(1-hydroxy-1-methylethyl)-1-oxido-pyridin-3-yl]phenyl}-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxylate

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Chemical Property of ethyl 1-{3-[6-(1-hydroxy-1-methylethyl)-1-oxido-pyridin-3-yl]phenyl}-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxylate

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Technology Process of ethyl 1-{3-[6-(1-hydroxy-1-methylethyl)-1-oxido-pyridin-3-yl]phenyl}-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxylate

There total 7 articles about ethyl 1-{3-[6-(1-hydroxy-1-methylethyl)-1-oxido-pyridin-3-yl]phenyl}-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

: 3-chloro-2-(1-hydroxy-1-methylethyl)-pyridine-N-oxide hydrochloride

: 694489-60-6
ethyl 1-(phenyl-3-dihydroxyboranyl)-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxylate

: 694489-61-7
ethyl 1-{3-[6-(1-hydroxy-1-methylethyl)-1-oxido-pyridin-3-yl]phenyl}-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxylate

Guidance literature:: With tri-tert-butyl phosphine; potassium carbonate; bis(η3-allyl-μ-chloropalladium(II)); In N,N-dimethyl acetamide; water; at 60 ℃; for 6h;
DOI:10.1016/j.tet.2005.03.143

Reference yield:

: 16110-09-1
2,5 dichloropyridine

: 694489-61-7
ethyl 1-{3-[6-(1-hydroxy-1-methylethyl)-1-oxido-pyridin-3-yl]phenyl}-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: triethylamine; dppf / palladium(II) acetate / 11 h / 100 °C / 2585.74 Torr

2.1: 89 percent / sodium chloride / tetrahydrofuran / 20 - 25 °C

3.1: urea-hydrogen peroxide; trifluoroacetic acid / ethyl acetate / -10 - 20 °C

3.2: 57 percent / hydrochloric acid / isopropyl acetate

4.1: 80 percent / potassium carbonate; tri-t-butylphosphine / [(allyl)PdCl]2 / H₂O; N,N-dimethyl-acetamide / 6 h / 60 °C

With 1,1'-bis-(diphenylphosphino)ferrocene; tri-tert-butyl phosphine; urea-hydrogen peroxide; potassium carbonate; triethylamine; trifluoroacetic acid; sodium chloride; bis(η3-allyl-μ-chloropalladium(II)); palladium diacetate; In tetrahydrofuran; N,N-dimethyl acetamide; water; ethyl acetate; 4.1: Suzuki-Miyaura cross-coupling;
DOI:10.1016/j.tet.2005.03.143

Reference yield:

: 49609-84-9
2-Chloronicotinoyl chloride

: 694489-61-7
ethyl 1-{3-[6-(1-hydroxy-1-methylethyl)-1-oxido-pyridin-3-yl]phenyl}-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: triethylamine / toluene / 5 h / 70 °C

1.2: 78 percent / potassium phosphate / N,N-dimethyl-acetamide / 18 h / 70 °C

2.1: 80 percent / potassium carbonate; tri-t-butylphosphine / [(allyl)PdCl]2 / H₂O; N,N-dimethyl-acetamide / 6 h / 60 °C

With tri-tert-butyl phosphine; potassium carbonate; triethylamine; bis(η3-allyl-μ-chloropalladium(II)); In N,N-dimethyl acetamide; water; toluene; 2.1: Suzuki-Miyaura cross-coupling;
DOI:10.1016/j.tet.2005.03.143