6-{1-[3-(benzyloxy)-2,2-difluoropropyl]-5-(4-fluorophenyl)-3-methyl-1H-pyrazol-4-yl}-2H-1,4-benzoxazin-3(4H)-one

Base Information

• Chemical Name: 6-{1-[3-(benzyloxy)-2,2-difluoropropyl]-5-(4-fluorophenyl)-3-methyl-1H-pyrazol-4-yl}-2H-1,4-benzoxazin-3(4H)-one
• CAS No.: 1221503-59-8
• Molecular Formula: C₂₈H₂₄F₃N₃O₃
• Molecular Weight: 507.512
• Mol file: 1221503-59-8.mol

Synonyms:6-{1-[3-(benzyloxy)-2,2-difluoropropyl]-5-(4-fluorophenyl)-3-methyl-1H-pyrazol-4-yl}-2H-1,4-benzoxazin-3(4H)-one

Chemical Property of 6-{1-[3-(benzyloxy)-2,2-difluoropropyl]-5-(4-fluorophenyl)-3-methyl-1H-pyrazol-4-yl}-2H-1,4-benzoxazin-3(4H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-{1-[3-(benzyloxy)-2,2-difluoropropyl]-5-(4-fluorophenyl)-3-methyl-1H-pyrazol-4-yl}-2H-1,4-benzoxazin-3(4H)-one

There total 8 articles about 6-{1-[3-(benzyloxy)-2,2-difluoropropyl]-5-(4-fluorophenyl)-3-methyl-1H-pyrazol-4-yl}-2H-1,4-benzoxazin-3(4H)-one 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: 61.0%

6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-benzo[b][1,4]oxazin-3(4H)-one (943994-02-3) + 1-[3-(benzyloxy)-2,2-difluoropropyl]-4-bromo-5-(4-fluorophenyl)-3-methyl-1H-pyrazole (1221503-45-2) → 6-{1-[3-(benzyloxy)-2,2-difluoropropyl]-5-(4-fluorophenyl)-3-methyl-1H-pyrazol-4-yl}-2H-1,4-benzoxazin-3(4H)-one (1221503-59-8)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; caesium carbonate; In tetrahydrofuran; water; for 24h; Inert atmosphere; Reflux;

DOI:10.1016/j.bmc.2014.07.038

Reference yield:

1-(benzyloxy)-3-[4-bromo-5-(4-fluorophenyl)-3-methyl-1H-pyrazol-1-yl]propan-2-ol (1221503-42-9) → 6-{1-[3-(benzyloxy)-2,2-difluoropropyl]-5-(4-fluorophenyl)-3-methyl-1H-pyrazol-4-yl}-2H-1,4-benzoxazin-3(4H)-one (1221503-59-8)

Guidance literature:

Multi-step reaction with 3 steps

1: Dess-Martin periodane / toluene / 12 h / 20 °C / Cooling with ice

2: diethylamino-sulfur trifluoride / toluene / 30 h / 40 °C / Cooling with ice

3: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / tetrahydrofuran; water / 24 h / Inert atmosphere; Reflux

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; diethylamino-sulfur trifluoride; caesium carbonate; Dess-Martin periodane; In tetrahydrofuran; water; toluene; 1: |Dess-Martin Oxidation / 3: |Suzuki Coupling;

DOI:10.1016/j.bmc.2014.07.038

Reference yield:

1-(benzyloxy)-3-[4-bromo-5-(4-fluorophenyl)-3-methyl-1H-pyrazol-1-yl]acetone (1221503-44-1) → 6-{1-[3-(benzyloxy)-2,2-difluoropropyl]-5-(4-fluorophenyl)-3-methyl-1H-pyrazol-4-yl}-2H-1,4-benzoxazin-3(4H)-one (1221503-59-8)

Guidance literature:

Multi-step reaction with 2 steps

1: diethylamino-sulfur trifluoride / toluene / 30 h / 40 °C / Cooling with ice

2: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / tetrahydrofuran; water / 24 h / Inert atmosphere; Reflux

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; diethylamino-sulfur trifluoride; caesium carbonate; In tetrahydrofuran; water; toluene; 2: |Suzuki Coupling;

DOI:10.1016/j.bmc.2014.07.038

upstream raw materials:

6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-benzo[b][1,4]oxazin-3(4H)-one

1-[3-(benzyloxy)-2,2-difluoropropyl]-4-bromo-5-(4-fluorophenyl)-3-methyl-1H-pyrazole

Benzyloxymethyl-oxiran

1-(benzyloxy)-3-hydrazinopropan-2-ol

Downstream raw materials:

6-[1-(2,2-difluoro-3-hydroxypropyl)-5-(4-fluorophenyl)-3-methyl-1H-pyrazol-4-yl]-2H-1,4-benzoxazin-3(4H)-one

2,2-Difluoro-3-[5-(4-fluorophenyl)-3-methyl-4-(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl)-1H-pyrazol-1-yl]propyl acetate