ethyl (2E)-3-[5-(4-chlorophenyl)-4-(2-formylphenyl)-1-phenyl-1H-pyrazol-3-yl]prop-2-enoate

Base Information

• Chemical Name: ethyl (2E)-3-[5-(4-chlorophenyl)-4-(2-formylphenyl)-1-phenyl-1H-pyrazol-3-yl]prop-2-enoate
• CAS No.: 1435483-39-8
• Molecular Formula: C₂₇H₂₁ClN₂O₃
• Molecular Weight: 456.928

Synonyms:ethyl (2E)-3-[5-(4-chlorophenyl)-4-(2-formylphenyl)-1-phenyl-1H-pyrazol-3-yl]prop-2-enoate

Chemical Property of ethyl (2E)-3-[5-(4-chlorophenyl)-4-(2-formylphenyl)-1-phenyl-1H-pyrazol-3-yl]prop-2-enoate

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Technology Process of ethyl (2E)-3-[5-(4-chlorophenyl)-4-(2-formylphenyl)-1-phenyl-1H-pyrazol-3-yl]prop-2-enoate

There total 2 articles about ethyl (2E)-3-[5-(4-chlorophenyl)-4-(2-formylphenyl)-1-phenyl-1H-pyrazol-3-yl]prop-2-enoate 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: 74.0%

ethyl (2E)-3-[5-(4-chlorophenyl)-4-iodo-1-phenyl-1H-pyrazol-3-yl]prop-2-enoate (1435483-50-3) + 2-formylbenzene boronic acid (40138-16-7) → ethyl (2E)-3-[5-(4-chlorophenyl)-4-(2-formylphenyl)-1-phenyl-1H-pyrazol-3-yl]prop-2-enoate (1435483-39-8)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In N,N-dimethyl-formamide; at 90 ℃; for 3h; Inert atmosphere;

DOI:10.1016/j.tet.2013.03.099

Reference yield:

5-(4-chlorophenyl)-4-iodo-1-phenyl-3(1H)-pyrazolecarbaldehyde (1002102-41-1) → ethyl (2E)-3-[5-(4-chlorophenyl)-4-(2-formylphenyl)-1-phenyl-1H-pyrazol-3-yl]prop-2-enoate (1435483-39-8)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydride / tetrahydrofuran / 6 h / 0 - 20 °C

2: sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 3 h / 90 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydride; sodium carbonate; In tetrahydrofuran; N,N-dimethyl-formamide; 1: |Horner-Wadsworth-Emmons Olefination / 2: |Suzuki Coupling;

DOI:10.1016/j.tet.2013.03.099

Reference yield: 91.0%

sarcosine (107-97-1,25951-24-0) + ethyl (2E)-3-[5-(4-chlorophenyl)-4-(2-formylphenyl)-1-phenyl-1H-pyrazol-3-yl]prop-2-enoate (1435483-39-8) → ethyl rac-(2S,6R)-10-(4-chlorophenyl)-3-methyl-9-phenyl-3,8,9-triazatetracyclo[10.4.0.02,6.07,11]hexadeca-1(16),7,10,12,14-pentaene-5-carboxylate + ethyl rac-(2R,6R)-10-(4-chlorophenyl)-3-methyl-9-phenyl-3,8,9-triazatetracyclo[10.4.0.02,6.07,11]hexadeca-1(16),7,10,12,14-pentaene-5-carboxylate

Guidance literature:

In toluene; at 110 ℃; for 3h; diastereoselective reaction;

DOI:10.1016/j.tet.2013.03.099

upstream raw materials:

ethyl (2E)-3-[5-(4-chlorophenyl)-4-iodo-1-phenyl-1H-pyrazol-3-yl]prop-2-enoate

2-formylbenzene boronic acid

5-(4-chlorophenyl)-4-iodo-1-phenyl-3(1H)-pyrazolecarbaldehyde

Downstream raw materials:

ethyl 10-(4-chlorophenyl)-9-phenyl-4-oxa-3,8,9-triazatetracyclo[10.4.0.0^2,6.0^7,11]hexadeca-1⁽¹⁶⁾,2,5,7,10,12,14-heptaene-5-carboxylate

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