4-[(5-methyl-3-{3-[4-(1,1,1-trifluoro-2-methylpropan-2-yl)-phenyl]-1,2,4-oxadiazol-5-yl}-1H-pyrazol-1-yl)methyl]aniline

Base Information

• Chemical Name: 4-[(5-methyl-3-{3-[4-(1,1,1-trifluoro-2-methylpropan-2-yl)-phenyl]-1,2,4-oxadiazol-5-yl}-1H-pyrazol-1-yl)methyl]aniline
• CAS No.: 1574556-41-4
• Molecular Formula: C₂₃H₂₂F₃N₅O
• Molecular Weight: 441.456

Synonyms:4-[(5-methyl-3-{3-[4-(1,1,1-trifluoro-2-methylpropan-2-yl)-phenyl]-1,2,4-oxadiazol-5-yl}-1H-pyrazol-1-yl)methyl]aniline

Chemical Property of 4-[(5-methyl-3-{3-[4-(1,1,1-trifluoro-2-methylpropan-2-yl)-phenyl]-1,2,4-oxadiazol-5-yl}-1H-pyrazol-1-yl)methyl]aniline

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Technology Process of 4-[(5-methyl-3-{3-[4-(1,1,1-trifluoro-2-methylpropan-2-yl)-phenyl]-1,2,4-oxadiazol-5-yl}-1H-pyrazol-1-yl)methyl]aniline

There total 10 articles about 4-[(5-methyl-3-{3-[4-(1,1,1-trifluoro-2-methylpropan-2-yl)-phenyl]-1,2,4-oxadiazol-5-yl}-1H-pyrazol-1-yl)methyl]aniline 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: 55.0%

5-[5-methyl-1-(4-nitrobenzyl)-1H-pyrazol-3-yl]-3-[4-(1,1,1-trifluoro-2-methylpropan-2-yl)phenyl]-1,2,4-oxadiazole (1574556-40-3) → 4-[(5-methyl-3-{3-[4-(1,1,1-trifluoro-2-methylpropan-2-yl)-phenyl]-1,2,4-oxadiazol-5-yl}-1H-pyrazol-1-yl)methyl]aniline (1574556-41-4)

Guidance literature:

With indium; ammonium chloride; In ethanol; water; for 12h; Reflux;

DOI:10.1002/cmdc.201300357

Reference yield:

4-nitrobenzyl chloride (619-73-8) → 4-[(5-methyl-3-{3-[4-(1,1,1-trifluoro-2-methylpropan-2-yl)-phenyl]-1,2,4-oxadiazol-5-yl}-1H-pyrazol-1-yl)methyl]aniline (1574556-41-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: triethylamine / tetrahydrofuran / 0.5 h / 15 °C / Cooling with ice

2.1: potassium tert-butylate / tetrahydrofuran / 0.17 h / 0 °C

2.2: 16 h / 20 °C

3.1: indium; ammonium chloride / ethanol; water / 12 h / Reflux

With indium; potassium tert-butylate; ammonium chloride; triethylamine; In tetrahydrofuran; ethanol; water;

DOI:10.1002/cmdc.201300357

Reference yield:

2‐(4‐bromophenyl)‐1,1,1‐trifluoropropan‐2‐ol (122243-28-1) → 4-[(5-methyl-3-{3-[4-(1,1,1-trifluoro-2-methylpropan-2-yl)-phenyl]-1,2,4-oxadiazol-5-yl}-1H-pyrazol-1-yl)methyl]aniline (1574556-41-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 1.5 h / 20 - 40 °C / Inert atmosphere

1.2: 1 h / 40 °C / Inert atmosphere

2.1: dichloromethane; n-heptane / 1.5 h / 0 - 20 °C

3.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 16 h / 80 °C / Inert atmosphere

4.1: triethylamine; hydroxylamine hydrochloride / ethanol / 1 h / Reflux

5.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 7 h / 20 - 140 °C

6.1: potassium tert-butylate / tetrahydrofuran / 0.17 h / 0 °C

6.2: 16 h / 20 °C

7.1: indium; ammonium chloride / ethanol; water / 12 h / Reflux

With indium; tetrakis(triphenylphosphine) palladium⁽⁰⁾; hydroxylamine hydrochloride; potassium tert-butylate; sodium hydride; ammonium chloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; ethanol; n-heptane; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;

DOI:10.1002/cmdc.201300357

upstream raw materials:

4-nitrobenzyl methanesulfonate

4-nitrobenzyl chloride

2‐(4‐bromophenyl)‐1,1,1‐trifluoropropan‐2‐ol

4'-bromo-2,2,2-trifluoroacetophenone

Downstream raw materials:

N-methyl-4-[(5-methyl-3-{3-[4-(1,1,1-trifluoro-2-methylpropan-2-yl)phenyl]-1,2,4-oxadiazol-5-yl}-1H-pyrazol-1-yl)methyl]aniline

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