7-(3,5-difluorophenoxy)-4,5,6,7-tetrahydro-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-1,2-benzisoxazole

Base Information

• Chemical Name: 7-(3,5-difluorophenoxy)-4,5,6,7-tetrahydro-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-1,2-benzisoxazole
• CAS No.: 1433663-33-2
• Molecular Formula: C₂₄H₂₁F₂N₃O₃
• Molecular Weight: 437.446

Synonyms:7-(3,5-difluorophenoxy)-4,5,6,7-tetrahydro-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-1,2-benzisoxazole

Chemical Property of 7-(3,5-difluorophenoxy)-4,5,6,7-tetrahydro-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-1,2-benzisoxazole

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Technology Process of 7-(3,5-difluorophenoxy)-4,5,6,7-tetrahydro-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-1,2-benzisoxazole

There total 10 articles about 7-(3,5-difluorophenoxy)-4,5,6,7-tetrahydro-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-1,2-benzisoxazole 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: 57.0%

3,5-difluorophenol (2713-34-0) + 3-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-4,5,6,7-tetrahydrobenzo[d]isoxazol-7-ol (1433663-81-0) → 7-(3,5-difluorophenoxy)-4,5,6,7-tetrahydro-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-1,2-benzisoxazole (1433663-33-2)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 50 ℃; Inert atmosphere;

DOI:10.1021/acsmedchemlett.7b00178

Reference yield:

3-(3-methoxy-4-nitrophenyl)-5,6-dihydrobenzo[d]isoxazol-7(4H)-one (1433663-58-1) → 7-(3,5-difluorophenoxy)-4,5,6,7-tetrahydro-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-1,2-benzisoxazole (1433663-33-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: tin(ll) chloride / ethanol / 2 h / 55 °C / Inert atmosphere

2.1: acetic anhydride / 1 h / Inert atmosphere; Cooling

2.2: 2 h / Inert atmosphere; Cooling

3.1: potassium iodide; caesium carbonate / 55 °C / Inert atmosphere

4.1: acetic acid; ammonium acetate / 95 °C / Inert atmosphere

5.1: sodium tetrahydroborate / ethanol; tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

6.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 50 °C / Inert atmosphere

With sodium tetrahydroborate; ammonium acetate; acetic anhydride; caesium carbonate; acetic acid; triphenylphosphine; potassium iodide; tin(ll) chloride; diethylazodicarboxylate; In tetrahydrofuran; ethanol; 6.1: |Mitsunobu Displacement;

DOI:10.1021/acsmedchemlett.7b00178

Reference yield:

N-(2-methoxy-4-(7-oxo-4,5,6,7-tetrahydrobenzo[d]isoxazol-3-yl)phenyl)formamide (1433663-66-1) → 7-(3,5-difluorophenoxy)-4,5,6,7-tetrahydro-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-1,2-benzisoxazole (1433663-33-2)

Guidance literature:

Multi-step reaction with 4 steps

1: potassium iodide; caesium carbonate / 55 °C / Inert atmosphere

2: acetic acid; ammonium acetate / 95 °C / Inert atmosphere

3: sodium tetrahydroborate / ethanol; tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

4: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 50 °C / Inert atmosphere

With sodium tetrahydroborate; ammonium acetate; caesium carbonate; acetic acid; triphenylphosphine; potassium iodide; diethylazodicarboxylate; In tetrahydrofuran; ethanol; 4: |Mitsunobu Displacement;

DOI:10.1021/acsmedchemlett.7b00178

upstream raw materials:

3-(3-methoxy-4-nitrophenyl)-5,6-dihydrobenzo[d]isoxazol-7(4H)-one

3-(4-amino-3-methoxyphenyl)-5,6-dihydrobenzo[d]isoxazol-7(4H)-one

N-(2-methoxy-4-(7-oxo-4,5,6,7-tetrahydrobenzo[d]isoxazol-3-yl)phenyl)formamide

N-(2-methoxy-4-(7-oxo-4,5,6,7-tetrahydrobenzo[d]isoxazol-3-yl)phenyl)-N-(2-oxopropyl)formamide

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