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ethyl 2-hydroxy-2,2-dimethylethanoate
2-((1-benzyl-1H-indazol-3-yl)methoxy)-2-methylpropanoic acid
Conditions | Yield |
---|---|
Stage #1: ethyl 2-hydroxy-2,2-dimethylethanoate With sodium hexamethyldisilazane In tetrahydrofuran; N,N-dimethyl-formamide at 0 - 5℃; for 1.5h; Inert atmosphere; Stage #2: 1-benzyl-3-chloromethyl-1H-indazole With tetra-(n-butyl)ammonium iodide In tetrahydrofuran; N,N-dimethyl-formamide at 0 - 25℃; for 10h; Inert atmosphere; | 88.7% |
benzyl bromide
2-((1-benzyl-1H-indazol-3-yl)methoxy)-2-methylpropanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: potassium tert-butylate / toluene / 0.5 h / 20 °C / Inert atmosphere 1.2: 4.5 h / 20 °C 2.1: isopropylmagnesium chloride / tetrahydrofuran / 7 h / -10 °C / Inert atmosphere 2.2: 0 °C 3.1: hydrogenchloride / toluene; water / 2 h / 90 °C 4.1: sodium hydride / N,N-dimethyl-formamide; toluene / 1.5 h / Inert atmosphere 4.2: 10 h / 90 °C 5.1: sodium hydroxide / 3 h / Reflux View Scheme | |
Multi-step reaction with 5 steps 1.1: potassium tert-butylate / toluene / 0.5 h / 20 °C / Inert atmosphere 1.2: 4.5 h / 20 °C 2.1: isopropylmagnesium chloride / tetrahydrofuran / 7 h / -10 °C / Inert atmosphere 2.2: 2 h / 0 °C 3.1: hydrogenchloride / toluene; water / 2 h / 90 °C 4.1: sodium hydride / toluene; mineral oil / 1.5 h / Inert atmosphere 4.2: 10 h / 90 °C 5.1: sodium hydroxide / 3 h / Reflux View Scheme |
3-bromo-1H-indazole
2-((1-benzyl-1H-indazol-3-yl)methoxy)-2-methylpropanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: potassium tert-butylate / toluene / 0.5 h / 20 °C / Inert atmosphere 1.2: 4.5 h / 20 °C 2.1: isopropylmagnesium chloride / tetrahydrofuran / 7 h / -10 °C / Inert atmosphere 2.2: 0 °C 3.1: hydrogenchloride / toluene; water / 2 h / 90 °C 4.1: sodium hydride / N,N-dimethyl-formamide; toluene / 1.5 h / Inert atmosphere 4.2: 10 h / 90 °C 5.1: sodium hydroxide / 3 h / Reflux View Scheme | |
Multi-step reaction with 5 steps 1.1: potassium tert-butylate / toluene / 0.5 h / 20 °C / Inert atmosphere 1.2: 4.5 h / 20 °C 2.1: isopropylmagnesium chloride / tetrahydrofuran / 7 h / -10 °C / Inert atmosphere 2.2: 2 h / 0 °C 3.1: hydrogenchloride / toluene; water / 2 h / 90 °C 4.1: sodium hydride / toluene; mineral oil / 1.5 h / Inert atmosphere 4.2: 10 h / 90 °C 5.1: sodium hydroxide / 3 h / Reflux View Scheme |
(1-Benzyl-1H-indazol-3-yl)-methanol
2-((1-benzyl-1H-indazol-3-yl)methoxy)-2-methylpropanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: hydrogenchloride / toluene; water / 2 h / 90 °C 2.1: sodium hydride / N,N-dimethyl-formamide; toluene / 1.5 h / Inert atmosphere 2.2: 10 h / 90 °C 3.1: sodium hydroxide / 3 h / Reflux View Scheme | |
Multi-step reaction with 3 steps 1.1: hydrogenchloride / toluene; water / 2 h / 90 °C 2.1: sodium hydride / toluene; mineral oil / 1.5 h / Inert atmosphere 2.2: 10 h / 90 °C 3.1: sodium hydroxide / 3 h / Reflux View Scheme |
2-((1-benzyl-1H-indazol-3-yl)methoxy)-2-methylpropanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide; toluene / 1.5 h / Inert atmosphere 1.2: 10 h / 90 °C 2.1: sodium hydroxide / 3 h / Reflux View Scheme | |
Multi-step reaction with 2 steps 1.1: sodium hydride / toluene; mineral oil / 1.5 h / Inert atmosphere 1.2: 10 h / 90 °C 2.1: sodium hydroxide / 3 h / Reflux View Scheme |
N-benzyl-3-iodo-1H-indazole
2-((1-benzyl-1H-indazol-3-yl)methoxy)-2-methylpropanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: isopropylmagnesium chloride / 2-methyltetrahydrofuran / 2 h / -10 °C / Inert atmosphere 1.2: 2 h / 0 °C 2.1: hydrogenchloride / toluene; water / 2 h / 90 °C 3.1: sodium hydride / N,N-dimethyl-formamide; toluene / 1.5 h / Inert atmosphere 3.2: 10 h / 90 °C 4.1: sodium hydroxide / 3 h / Reflux View Scheme | |
Multi-step reaction with 5 steps 1.1: isopropylmagnesium chloride / tetrahydrofuran / 2 h / -10 °C / Inert atmosphere 1.2: 0 °C 2.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 0.25 h / 20 °C / Inert atmosphere 3.1: hydrogenchloride / toluene; water / 2 h / 90 °C 4.1: sodium hydride / N,N-dimethyl-formamide; toluene / 1.5 h / Inert atmosphere 4.2: 10 h / 90 °C 5.1: sodium hydroxide / 3 h / Reflux View Scheme | |
Multi-step reaction with 4 steps 1.1: isopropylmagnesium chloride / 2-methyltetrahydrofuran / 2 h / -10 °C / Inert atmosphere 1.2: 2 h / 0 °C 2.1: hydrogenchloride / toluene; water / 2 h / 90 °C 3.1: sodium hydride / toluene; mineral oil / 1.5 h / Inert atmosphere 3.2: 10 h / 90 °C 4.1: sodium hydroxide / 3 h / Reflux View Scheme | |
Multi-step reaction with 5 steps 1.1: isopropylmagnesium chloride / tetrahydrofuran / 2 h / -10 °C / Inert atmosphere 1.2: 0 °C 2.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 0.25 h / 20 °C / Inert atmosphere 3.1: hydrogenchloride / toluene; water / 2 h / 90 °C 4.1: sodium hydride / toluene; mineral oil / 1.5 h / Inert atmosphere 4.2: 10 h / 90 °C 5.1: sodium hydroxide / 3 h / Reflux View Scheme |
1-benzyl-1H-indazole-3-carbaldehyde
2-((1-benzyl-1H-indazol-3-yl)methoxy)-2-methylpropanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 0.25 h / 20 °C / Inert atmosphere 2.1: hydrogenchloride / toluene; water / 2 h / 90 °C 3.1: sodium hydride / N,N-dimethyl-formamide; toluene / 1.5 h / Inert atmosphere 3.2: 10 h / 90 °C 4.1: sodium hydroxide / 3 h / Reflux View Scheme | |
Multi-step reaction with 4 steps 1.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 0.25 h / 20 °C / Inert atmosphere 2.1: hydrogenchloride / toluene; water / 2 h / 90 °C 3.1: sodium hydride / toluene; mineral oil / 1.5 h / Inert atmosphere 3.2: 10 h / 90 °C 4.1: sodium hydroxide / 3 h / Reflux View Scheme |
2-((1-benzyl-1H-indazol-3-yl)methoxy)-2-methylpropanoic acid
Conditions | Yield |
---|---|
Stage #1: C21H24N2O3 With sodium hydroxide for 3h; Reflux; Stage #2: With hydrogenchloride In water | |
Stage #1: C21H24N2O3 With sodium hydroxide for 3h; Reflux; Stage #2: With hydrogenchloride In water |
1-benzyl-3-bromoindazole
2-((1-benzyl-1H-indazol-3-yl)methoxy)-2-methylpropanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: isopropylmagnesium chloride / tetrahydrofuran / 7 h / -10 °C / Inert atmosphere 1.2: 0 °C 2.1: hydrogenchloride / toluene; water / 2 h / 90 °C 3.1: sodium hydride / N,N-dimethyl-formamide; toluene / 1.5 h / Inert atmosphere 3.2: 10 h / 90 °C 4.1: sodium hydroxide / 3 h / Reflux View Scheme | |
Multi-step reaction with 4 steps 1.1: isopropylmagnesium chloride / tetrahydrofuran / 7 h / -10 °C / Inert atmosphere 1.2: 2 h / 0 °C 2.1: hydrogenchloride / toluene; water / 2 h / 90 °C 3.1: sodium hydride / toluene; mineral oil / 1.5 h / Inert atmosphere 3.2: 10 h / 90 °C 4.1: sodium hydroxide / 3 h / Reflux View Scheme |
morpholine
2-((1-benzyl-1H-indazol-3-yl)methoxy)-2-methylpropanoic acid
1-benzyl-3-[(1,1-dimethyl-2-morpholin-4-yl-2-oxyethoxy)methyl]-1H-indazole
Conditions | Yield |
---|---|
Stage #1: 2-((1-benzylindazol-3-yl)methoxy)-2-methyl propionic acid With sodium methylate In methanol at 20℃; for 0.166667h; Stage #2: morpholine With thionyl chloride In toluene at 20℃; |
2-((1-benzyl-1H-indazol-3-yl)methoxy)-2-methylpropanoic acid
2-[(1-benzyl-1H-indazol-3-yl)methoxy]-2-methylpropan-1-ol
Conditions | Yield |
---|---|
Stage #1: 2-((1-benzylindazol-3-yl)methoxy)-2-methyl propionic acid With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether at 20℃; Stage #2: With water; sodium hydroxide In tetrahydrofuran; diethyl ether |
2-((1-benzyl-1H-indazol-3-yl)methoxy)-2-methylpropanoic acid
2-[(1-benzyl-5-chloro-1H-indazol-3-yl)methoxy]-2-methylpropanoic acid
Conditions | Yield |
---|---|
With chlorine; acetic acid at 20℃; |
2-((1-benzyl-1H-indazol-3-yl)methoxy)-2-methylpropanoic acid
2-[(1-benzyl-5-bromo-1H-indazol-3-yl)methoxy]-2-methylpropanoic acid
Conditions | Yield |
---|---|
With bromine; acetic acid at 10 - 20℃; |
2-((1-benzyl-1H-indazol-3-yl)methoxy)-2-methylpropanoic acid
1-benzyl-3-[(1,1-dimethyl-2-morpholin-4-ylethoxy)methyl]-1H-indazole.
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: sodium methylate / methanol / 0.17 h / 20 °C 1.2: 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 20 °C / Reflux View Scheme |
2-((1-benzyl-1H-indazol-3-yl)methoxy)-2-methylpropanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: sodium methylate / methanol / 0.17 h / 20 °C 1.2: 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 20 °C / Reflux 3.1: ethanol / 20 °C View Scheme |
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