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With lithium trifluoromethanesulfonate In acetonitrile at 50℃;
5.3
Step 3: Preparation of (R)-methyl 3-(l-ethyl-lH-indazol-5-ylamino)-2-hydroxypropanoate.(R)-Methyl oxirane-2-carboxylate (1.11 mL, 0.0127 mol), l-ethyl-lH-indazol-5- amine (2.05 g, 0.0127 mol) and lithium trifluoromethanesulfonate (1.98 g, 0.0127 mol) in acetonitrile (25 mL) are stirred and heated at 50 0C overnight. The reaction is diluted with ethyl acetate, washed with water and brine, the organic layer dried (Mg2SO4) and evaporated. The residue is purified by flash chromatography (50% EtOAc/Hexanes) to give the title compound (0.735 g, 22%); HPLC (SYMMETRY C18 3.5 μM, 4.6 x 30 mm column; gradient elution 2%-98% MeCN with 0.1% TFA over 10 min; 2 mL/min rate): retention time = 2.80 min; MS for C13H17N3O3InZz 264.3(M+H)+.
With iron; ammonium chloride In ethanol; water at 80℃; for 1h;
5.2
Step 2: Preparation of 1 -ethyl- lH-indazol-5-amine.Iron powder (5.17 g, 0.0926 mol) is added to a solution of l-ethyl-5-nitro-lH- indazole (4.75 g, 0.0231 mol) and ammonium chloride (12.4 g, 0.231 mol) in ethanol (175 mL) and water (75 mL) at 80 0C. The mixture is vigorously stirred and heated for 1 hour, diluted with dichloromethane (500 mL) and filtered. The organic layer is separated, dried (Mg2SO4) and evaporated to afford the title compound (4.06 g, 99%); HPLC (SYMMETRY Ci8 3.5 μM, 4.6 x 30 mm column; gradient elution 2%-98% MeCN with 0.1% TFA over 10 min; 2 mL/min rate): retention time = 2.52 min; MS for C9HϖN3m/z 162.2(M+H)+.
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