1-[7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]-4-(tetrahydro-2H-pyran-2-yloxy)-2-butyn-1-ol

Base Information

• Chemical Name: 1-[7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]-4-(tetrahydro-2H-pyran-2-yloxy)-2-butyn-1-ol
• CAS No.: 437612-92-5
• Molecular Formula: C₂₂H₂₀ClFN₂O₃
• Molecular Weight: 414.864

Synonyms:1-[7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]-4-(tetrahydro-2H-pyran-2-yloxy)-2-butyn-1-ol

Chemical Property of 1-[7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]-4-(tetrahydro-2H-pyran-2-yloxy)-2-butyn-1-ol

Chemical Property:

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Technology Process of 1-[7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]-4-(tetrahydro-2H-pyran-2-yloxy)-2-butyn-1-ol

There total 7 articles about 1-[7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]-4-(tetrahydro-2H-pyran-2-yloxy)-2-butyn-1-ol 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: 99.0%

3-(tetrahydropyran-2'-yloxy)propyne (6089-04-9) + 7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridine-3-carbaldehyde (437612-89-0) → 1-[7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]-4-(tetrahydro-2H-pyran-2-yloxy)-2-butyn-1-ol (437612-92-5)

Guidance literature:

3-(tetrahydropyran-2'-yloxy)propyne; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 0 ℃;

7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridine-3-carbaldehyde; In tetrahydrofuran; hexane; at -78 - 0 ℃;

DOI:10.1016/j.tet.2003.02.003

Reference yield:

6-chloro-2-picoline (18368-63-3) → 1-[7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]-4-(tetrahydro-2H-pyran-2-yloxy)-2-butyn-1-ol (437612-92-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 66 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / 15 h / 45 °C

2.1: 86 percent / hydroxylamine hydrochloride; aq. NaOH / methanol / 2 h / Heating

3.1: 1,2-dimethoxy-ethane / 0 - 15 °C

4.1: Et₃N / 1,2-dimethoxy-ethane / 2 h / 4 - 20 °C

5.1: 69.7 g / FeCl₂ / 1,2-dimethoxy-ethane / 3 h / Heating

6.1: 95 percent / POCl₃ / 1 h / 20 °C

7.1: n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C

7.2: 99 percent / tetrahydrofuran; hexane / -78 - 0 °C

With sodium hydroxide; n-butyllithium; hydroxylamine hydrochloride; triethylamine; iron(II) chloride; lithium hexamethyldisilazane; trichlorophosphate; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; hexane;

DOI:10.1016/j.tet.2003.02.003

Reference yield:

4-fluorobenzoic acid ethyl ester (451-46-7) → 1-[7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]-4-(tetrahydro-2H-pyran-2-yloxy)-2-butyn-1-ol (437612-92-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 66 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / 15 h / 45 °C

2.1: 86 percent / hydroxylamine hydrochloride; aq. NaOH / methanol / 2 h / Heating

3.1: 1,2-dimethoxy-ethane / 0 - 15 °C

4.1: Et₃N / 1,2-dimethoxy-ethane / 2 h / 4 - 20 °C

5.1: 69.7 g / FeCl₂ / 1,2-dimethoxy-ethane / 3 h / Heating

6.1: 95 percent / POCl₃ / 1 h / 20 °C

7.1: n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C

7.2: 99 percent / tetrahydrofuran; hexane / -78 - 0 °C

With sodium hydroxide; n-butyllithium; hydroxylamine hydrochloride; triethylamine; iron(II) chloride; lithium hexamethyldisilazane; trichlorophosphate; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; hexane;

DOI:10.1016/j.tet.2003.02.003

upstream raw materials:

3-(tetrahydropyran-2'-yloxy)propyne

7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridine-3-carbaldehyde

6-chloro-2-picoline

4-fluorobenzoic acid ethyl ester

Downstream raw materials:

4-[7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-cyclopentyl-6-[(tetrahydro-2H-pyran-2-yloxy)methyl]-2-pyrimidinamine

1-[7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]-4-(tetrahydro-2H-pyran-2-yloxy)-2-butyn-1-one

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