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

Base Information

Chemical Name:(6S)-2-nitro-6-({6-[4-trifluoromethoxyphenyl]-3-pyridinyl}oxy)-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine
CAS No.:1333170-62-9
Molecular Formula:C₁₈H₁₃F₃N₄O₅
Molecular Weight:422.32
Hs Code.:

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

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Chemical Property of (6S)-2-nitro-6-({6-[4-trifluoromethoxyphenyl]-3-pyridinyl}oxy)-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine

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Technology Process of (6S)-2-nitro-6-({6-[4-trifluoromethoxyphenyl]-3-pyridinyl}oxy)-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine

There total 6 articles about (6S)-2-nitro-6-({6-[4-trifluoromethoxyphenyl]-3-pyridinyl}oxy)-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: 79.0%

: 1333171-58-6
(6S)-6-[6-bromo-3-pyridinyloxy]-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine

: 139301-27-2
4-trifluoromethoxyphenylboronic acid

: 1333170-62-9
(6S)-2-nitro-6-({6-[4-trifluoromethoxyphenyl]-3-pyridinyl}oxy)-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine

Guidance literature:: With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In ethanol; water; N,N-dimethyl-formamide; toluene; at 90 ℃; for 3h; Inert atmosphere;
DOI:10.1021/jm200377r

Reference yield:

: 1333171-53-1
2-bromo-5-({(2S)-1-[(4-methoxybenzyl)oxy]-3-[(triisopropylsilyl)oxy]propan-2-yl}oxy)pyridine

: 1333170-62-9
(6S)-2-nitro-6-({6-[4-trifluoromethoxyphenyl]-3-pyridinyl}oxy)-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine

Guidance literature:: Multi-step reaction with 6 steps

1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 5 h / 20 °C

2: 1H-imidazole; iodine; triphenylphosphine / benzene / 1 h / 20 °C

3: potassium carbonate / N,N-dimethyl-formamide / 46 h / 81 - 92 °C

4: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

5: sodium hydride / N,N-dimethyl-formamide; mineral oil / 2.5 h / 0 - 20 °C / Inert atmosphere

6: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / ethanol; water; N,N-dimethyl-formamide; toluene / 3 h / 90 °C / Inert atmosphere

With 1H-imidazole; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrabutyl ammonium fluoride; iodine; sodium hydride; sodium carbonate; potassium carbonate; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; mineral oil; benzene; 6: Suzuki coupling;
DOI:10.1021/jm200377r

Reference yield:

: 1333171-54-2
(2S)-2-[6-bromo-3-pyridinyloxy]-3-[triisopropylsilyloxy]-1-propanol

: 1333170-62-9
(6S)-2-nitro-6-({6-[4-trifluoromethoxyphenyl]-3-pyridinyl}oxy)-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine

Guidance literature:: Multi-step reaction with 5 steps

1: 1H-imidazole; iodine; triphenylphosphine / benzene / 1 h / 20 °C

2: potassium carbonate / N,N-dimethyl-formamide / 46 h / 81 - 92 °C

3: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

4: sodium hydride / N,N-dimethyl-formamide; mineral oil / 2.5 h / 0 - 20 °C / Inert atmosphere

5: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / ethanol; water; N,N-dimethyl-formamide; toluene / 3 h / 90 °C / Inert atmosphere

With 1H-imidazole; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrabutyl ammonium fluoride; iodine; sodium hydride; sodium carbonate; potassium carbonate; triphenylphosphine; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide; toluene; mineral oil; benzene; 5: Suzuki coupling;
DOI:10.1021/jm200377r