methyl 2-{[4-(2-formylphenyl)-1,5-diphenyl-1H-pyrazol-3-yl]methyl}prop-2-enoate

Base Information

• Chemical Name: methyl 2-{[4-(2-formylphenyl)-1,5-diphenyl-1H-pyrazol-3-yl]methyl}prop-2-enoate
• CAS No.: 1435483-34-3
• Molecular Formula: C₂₇H₂₂N₂O₃
• Molecular Weight: 422.483

Synonyms:methyl 2-{[4-(2-formylphenyl)-1,5-diphenyl-1H-pyrazol-3-yl]methyl}prop-2-enoate

Chemical Property of methyl 2-{[4-(2-formylphenyl)-1,5-diphenyl-1H-pyrazol-3-yl]methyl}prop-2-enoate

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Technology Process of methyl 2-{[4-(2-formylphenyl)-1,5-diphenyl-1H-pyrazol-3-yl]methyl}prop-2-enoate

There total 2 articles about methyl 2-{[4-(2-formylphenyl)-1,5-diphenyl-1H-pyrazol-3-yl]methyl}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: 72.0%

methyl 2-[(4-iodo-1,5-diphenyl-1H-pyrazol-3-yl)methyl]acrylate (1214996-55-0) + 2-formylbenzene boronic acid (40138-16-7) → methyl 2-{[4-(2-formylphenyl)-1,5-diphenyl-1H-pyrazol-3-yl]methyl}prop-2-enoate (1435483-34-3)

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:

4-iodo-1,5-diphenyl-1H-pyrazole-3-carbaldehyde (1002102-39-7) → methyl 2-{[4-(2-formylphenyl)-1,5-diphenyl-1H-pyrazol-3-yl]methyl}prop-2-enoate (1435483-34-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 1,4-diaza-bicyclo[2.2.2]octane / 20 °C

1.2: 3 h / 20 °C

1.3: 1 h / 20 °C

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

With 1,4-diaza-bicyclo[2.2.2]octane; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In N,N-dimethyl-formamide; 2.1: |Suzuki Coupling;

DOI:10.1016/j.tet.2013.03.099

Reference yield: 88.0%

methyl 2-{[4-(2-formylphenyl)-1,5-diphenyl-1H-pyrazol-3-yl]methyl}prop-2-enoate (1435483-34-3) + L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7) → methyl rac-(1R,14R)-9,10-diphenyl-10,11,20-triazapentacyclo[12.6.0.02,7.08,12.016,20]icosa-2(7),3,5,8,11-pentaene-14-carboxylate

Guidance literature:

In toluene; at 110 ℃; diastereoselective reaction; Reflux;

DOI:10.1016/j.tet.2013.03.099

upstream raw materials:

4-iodo-1,5-diphenyl-1H-pyrazole-3-carbaldehyde

methyl 2-[(4-iodo-1,5-diphenyl-1H-pyrazol-3-yl)methyl]acrylate

2-formylbenzene boronic acid

Downstream raw materials:

methyl 10,11-diphenyl-4-oxa-3,9,10-triazatetracyclo[11.4.0.0^2,6.0^8,12]heptadeca-1⁽¹⁷⁾,2,8,11,13,15-hexaene-6-carboxylate

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