⁽⁶⁵⁾-6-{[2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]oxy}-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine

Base Information

• Chemical Name: ⁽⁶⁵⁾-6-{[2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]oxy}-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine
• CAS No.: 1263417-20-4
• Molecular Formula: C₁₉H₂₃BFN₃O₆
• Molecular Weight: 419.218

Synonyms:⁽⁶⁵⁾-6-{[2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]oxy}-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine

Chemical Property of ⁽⁶⁵⁾-6-{[2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]oxy}-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine

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Technology Process of ⁽⁶⁵⁾-6-{[2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]oxy}-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine

There total 3 articles about ⁽⁶⁵⁾-6-{[2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]oxy}-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine 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: 66.0%

(6S)-6-[(4-bromo-2-fluorobenzyl)oxy]-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (1188335-21-8) + bis(pinacol)diborane (73183-34-3) → (65)-6-{[2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]oxy}-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (1263417-20-4)

Guidance literature:

With potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In dimethyl sulfoxide; at 89 ℃; for 5h; Inert atmosphere;

Reference yield:

4-bromo-2-fluorobenzyl bromide (76283-09-5) → (65)-6-{[2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]oxy}-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (1263417-20-4)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydride / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

2: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / dimethyl sulfoxide / 5 h / 89 °C / Inert atmosphere

With potassium acetate; sodium hydride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In dimethyl sulfoxide; N,N-dimethyl-formamide;

Reference yield:

(S)‐2‐nitro‐6,7‐dihydro‐5H‐imidazo[2,1‐b][1,3]oxazin‐6‐ol (187235-08-1) → (65)-6-{[2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]oxy}-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (1263417-20-4)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydride / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

2: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / dimethyl sulfoxide / 5 h / 89 °C / Inert atmosphere

With potassium acetate; sodium hydride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In dimethyl sulfoxide; N,N-dimethyl-formamide;

upstream raw materials:

(6S)-6-[(4-bromo-2-fluorobenzyl)oxy]-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine

bis(pinacol)diborane

4-bromo-2-fluorobenzyl bromide

(S)‐2‐nitro‐6,7‐dihydro‐5H‐imidazo[2,1‐b][1,3]oxazin‐6‐ol

Downstream raw materials:

(6S)-6-({2-fluoro-4-[5-(trifluoromethyl)-2-pyridinyl]benzyl}oxy)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine

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