2-(4-chlorophenyl)-2,5-dihydro-7-[4-(3-hydroxyprop-1-yn-1-yl)phenyl]-6-methylpyrazolo[4,3-c]pyridin-3-one

Base Information

• Chemical Name: 2-(4-chlorophenyl)-2,5-dihydro-7-[4-(3-hydroxyprop-1-yn-1-yl)phenyl]-6-methylpyrazolo[4,3-c]pyridin-3-one
• CAS No.: 244637-81-8
• Molecular Formula: C₂₂H₁₆ClN₃O₂
• Molecular Weight: 389.841

Synonyms:2-(4-chlorophenyl)-2,5-dihydro-7-[4-(3-hydroxyprop-1-yn-1-yl)phenyl]-6-methylpyrazolo[4,3-c]pyridin-3-one

Chemical Property of 2-(4-chlorophenyl)-2,5-dihydro-7-[4-(3-hydroxyprop-1-yn-1-yl)phenyl]-6-methylpyrazolo[4,3-c]pyridin-3-one

Chemical Property:

Purity/Quality:

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Technology Process of 2-(4-chlorophenyl)-2,5-dihydro-7-[4-(3-hydroxyprop-1-yn-1-yl)phenyl]-6-methylpyrazolo[4,3-c]pyridin-3-one

There total 8 articles about 2-(4-chlorophenyl)-2,5-dihydro-7-[4-(3-hydroxyprop-1-yn-1-yl)phenyl]-6-methylpyrazolo[4,3-c]pyridin-3-one 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:

Ethyl 4-chloro-2-methyl-3-(4-nitrophenyl)-5-pyridinecarboxylate (244638-71-9) → 2-(4-chlorophenyl)-2,5-dihydro-7-[4-(3-hydroxyprop-1-yn-1-yl)phenyl]-6-methylpyrazolo[4,3-c]pyridin-3-one (244637-81-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: butan-1-ol / Heating

2.1: Cu(acac)2; NaBH₄ / ethanol

3.1: isoamyl nitrite; tetrafluoroboric acid / dimethylformamide

3.2: iodine; potassium iodide / dimethylsulfoxide

4.1: Pd(PPh₃)4; CuI; piperidine / 80 °C

With piperidine; copper acetylacetonate; sodium tetrahydroborate; copper(l) iodide; tetrafluoroboric acid; tetrakis(triphenylphosphine) palladium⁽⁰⁾; isopentyl nitrite; In ethanol; N,N-dimethyl-formamide; butan-1-ol; 4.1: Sonogashira coupling;

DOI:10.1016/j.bmcl.2005.08.006

Reference yield:

Ethyl 1,4-dihydro-2-methyl-3-(4-nitrophenyl)-4-oxo-5-pyridinecarboxylate (244638-70-8) → 2-(4-chlorophenyl)-2,5-dihydro-7-[4-(3-hydroxyprop-1-yn-1-yl)phenyl]-6-methylpyrazolo[4,3-c]pyridin-3-one (244637-81-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: phosphorus oxychloride / Heating

2.1: butan-1-ol / Heating

3.1: Cu(acac)2; NaBH₄ / ethanol

4.1: isoamyl nitrite; tetrafluoroboric acid / dimethylformamide

4.2: iodine; potassium iodide / dimethylsulfoxide

5.1: Pd(PPh₃)4; CuI; piperidine / 80 °C

With piperidine; copper acetylacetonate; sodium tetrahydroborate; copper(l) iodide; tetrafluoroboric acid; tetrakis(triphenylphosphine) palladium⁽⁰⁾; trichlorophosphate; isopentyl nitrite; In ethanol; N,N-dimethyl-formamide; butan-1-ol; 5.1: Sonogashira coupling;

DOI:10.1016/j.bmcl.2005.08.006

Reference yield:

2-{[(Z)-1-Methyl-2-(4-nitro-phenyl)-vinylamino]-methylene}-malonic acid diethyl ester (868363-14-8) → 2-(4-chlorophenyl)-2,5-dihydro-7-[4-(3-hydroxyprop-1-yn-1-yl)phenyl]-6-methylpyrazolo[4,3-c]pyridin-3-one (244637-81-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: diphenyl ether; various solvent(s) / Heating

2.1: phosphorus oxychloride / Heating

3.1: butan-1-ol / Heating

4.1: Cu(acac)2; NaBH₄ / ethanol

5.1: isoamyl nitrite; tetrafluoroboric acid / dimethylformamide

5.2: iodine; potassium iodide / dimethylsulfoxide

6.1: Pd(PPh₃)4; CuI; piperidine / 80 °C

With piperidine; copper acetylacetonate; sodium tetrahydroborate; copper(l) iodide; tetrafluoroboric acid; tetrakis(triphenylphosphine) palladium⁽⁰⁾; trichlorophosphate; isopentyl nitrite; In diphenylether; ethanol; N,N-dimethyl-formamide; butan-1-ol; 6.1: Sonogashira coupling;

DOI:10.1016/j.bmcl.2005.08.006

upstream raw materials:

2-(4-chlorophenyl)-2,5-dihydro-7-(4-iodophenyl)-6-methylpyrazolo[4,3-c]pyridin-3-one

propargyl alcohol

Ethyl 4-chloro-2-methyl-3-(4-nitrophenyl)-5-pyridinecarboxylate

Ethyl 1,4-dihydro-2-methyl-3-(4-nitrophenyl)-4-oxo-5-pyridinecarboxylate

Downstream raw materials:

methanesulfonic acid 3-{4-[2-(4-chloro-phenyl)-6-methyl-3-oxo-3,5-dihydro-2H-pyrazolo[4,3-c]pyridin-7-yl]-phenyl}-prop-2-ynyl ester

2-(4-Chlorophenyl)-7-[4-(3-chloroprop-1-yn-1-yl)phenyl]-2,5-dihydro-6-methylpyrazolo[4,3-c]pyridin-3-one

7-[4-(3-azido-prop-1-ynyl)-phenyl]-2-(4-chloro-phenyl)-6-methyl-2,5-dihydro-pyrazolo[4,3-c]pyridin-3-one

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