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methyl 1-(4-(tert-butoxycarbonyl)phenyl)-3-iodo-1H-indazole-5-carboxylate[ No CAS ]
1-(4-(tert-butoxycarbonyl)phenyl)-3-iodo-1H-indazole-5-carboxylic acid[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
19.7%; 26.1%
With 1-methyl-pyrrolidin-2-one; caesium carbonate; at 120℃; for 16h;Inert atmosphere;
Methyl 3-iodo-1H-indazole-5-carboxylate (11.2 g; 37.1 mmol; 1.00 eq.), 1-methyl-2-pyrrolidinone (60.0ml), cesium carbonate (24.2 g; 74.2 mmol; 2.00 eq.) and 4-fluoro-benzoic acidtert-butyl ester (21.8 g; 111 mmol; 3.00 eq.) were stirred at 120 C for 16 hours in a round bottom flask. The reaction mixture was cooled, diluted in ethyl acetate (200 mL), washed with a saturated solution of NH4Cl (200 mL) and water (200 mL). The organic layer was dried over MgSO4, concentrated and purified by silica gel chromatography using heptane/ethyl acetate as eluent (1/1).Methyl 1-(4-(tert-butoxycarbonyl)phenyl)-3-iodo-1H-indazole-5-carboxylate was isolated as a beige solid (3.50 g; 19.7 %).MS-ESIm/z479 [MH+].1-(4-(tert-Butoxycarbonyl)phenyl)-3-iodo-1H-indazole-5-carboxylic acid was isolated as a yellow solid (4.50 g; 26.1 %)1H NMR (DMSO-d6) delta: 1.59 (s, 9H), 7.97 - 7.92 (m, 2H), 8.02 (d,J =9.3 Hz, 1H), 8.18 - 8.10 (m, 4H).MS-ESIm/z465 [MH+].
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