Technology Process of (3R,3aR,6R,6aR)-6-[[5-(4-bromophenyl)-6-chloro-1H-imidazo[4,5-b]pyridin-2-yl]oxy]-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-ol
There total 8 articles about (3R,3aR,6R,6aR)-6-[[5-(4-bromophenyl)-6-chloro-1H-imidazo[4,5-b]pyridin-2-yl]oxy]-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-ol which
guide to synthetic route it.
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synthetic route:
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1394373-61-5
(3R,3aR,6R,6aR)-6-[5-(4-bromophenyl)-6-chloro-1-(2-trimethylsilylethoxymethyl)imidazo[4,5-b]pyridin-2-yl]oxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-ol
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1394373-84-2
(3R,3aR,6R,6aR)-6-[[5-(4-bromophenyl)-6-chloro-1H-imidazo[4,5-b]pyridin-2-yl]oxy]-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-ol
- Guidance literature:
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With
potassium hydrogensulfate; formic acid;
In
water;
at 60 ℃;
Product distribution / selectivity;
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1394373-84-2
(3R,3aR,6R,6aR)-6-[[5-(4-bromophenyl)-6-chloro-1H-imidazo[4,5-b]pyridin-2-yl]oxy]-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-ol
- Guidance literature:
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Multi-step reaction with 10 steps
1.1: N-chloro-succinimide; acetic acid / 80 °C
2.1: sodium iodide; acetic acid / 2 h / 90 °C
3.1: ethanol / tin(II) chloride hydrate / 0.5 h / 70 °C
4.1: dmap / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere
5.1: potassium hydroxide / ethanol / 0.5 h / 20 °C
5.2: 1 h / 20 °C
6.1: Oxone / acetonitrile; water / 18 h / 20 °C
7.1: potassium dihydrogenphosphate / tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 17 h / 100 °C / Inert atmosphere
8.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 16 h / 20 °C / Cooling with ice
9.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 2.4 h / 20 °C
10.1: formic acid; potassium hydrogensulfate / water / 60 °C
With
Oxone; potassium hydrogensulfate; potassium dihydrogenphosphate; N-chloro-succinimide; formic acid; ethanol; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; sodium iodide; potassium hydroxide;
dmap; tetrakis(triphenylphosphine) palladium(0); tin(II) chloride hydrate;
In
tetrahydrofuran; 1,4-dioxane; ethanol; water; N,N-dimethyl-formamide; acetonitrile;
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1394373-84-2
(3R,3aR,6R,6aR)-6-[[5-(4-bromophenyl)-6-chloro-1H-imidazo[4,5-b]pyridin-2-yl]oxy]-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-ol
- Guidance literature:
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Multi-step reaction with 9 steps
1.1: sodium iodide; acetic acid / 2 h / 90 °C
2.1: ethanol / tin(II) chloride hydrate / 0.5 h / 70 °C
3.1: dmap / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere
4.1: potassium hydroxide / ethanol / 0.5 h / 20 °C
4.2: 1 h / 20 °C
5.1: Oxone / acetonitrile; water / 18 h / 20 °C
6.1: potassium dihydrogenphosphate / tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 17 h / 100 °C / Inert atmosphere
7.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 16 h / 20 °C / Cooling with ice
8.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 2.4 h / 20 °C
9.1: formic acid; potassium hydrogensulfate / water / 60 °C
With
Oxone; potassium hydrogensulfate; potassium dihydrogenphosphate; formic acid; ethanol; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; sodium iodide; potassium hydroxide;
dmap; tetrakis(triphenylphosphine) palladium(0); tin(II) chloride hydrate;
In
tetrahydrofuran; 1,4-dioxane; ethanol; water; N,N-dimethyl-formamide; acetonitrile;