甲基 2-氨基-5-氟-3-羟基苯甲酸甲酯

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of di(1H-imidazole-1-yl)methanamine (1.05 g, 6.52 mmol) in THF (30 mL) was added methyl-2-amino-5-fluoro-3-hydroxybenzoate (0.96 g, 5.22 mmol) at room temperature and the resulting reaction mixture was heated to reflux for 6 h. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was dissolved in EtOAc (200 mL) and washed with H2O (4×100 mL), saturated aqueous ammonium chloride (2×100 mL), brine (2×100 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure to afford methyl 2-amino-6-fluorobenzoxazole-4-carboxylate (0.95 g, 87%). 1H NMR and MS consistent. the resulting reaction mixture was heated to reflux for 6 h concentrated under reduced pressure The residue was dissolved in EtOAc (200 mL) washed with H2O (4×100 mL), saturated aqueous ammonium chloride (2×100 mL), brine (2×100 mL) dried over Na2SO4 filtered concentrated under reduced pressure

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of di(1H-imidazole-1-yl)methanamine (1.05 g, 6.52 mmol) in THF (30 mL) was added methyl-2-amino-5-fluoro-3-hydroxybenzoate (0.96 g, 5.22 mmol) at room temperature and the resulting reaction mixture was heated to reflux for 6 h. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was dissolved in EtOAc (200 mL) and washed with H2O (4×100 mL), saturated aqueous ammonium chloride (2×100 mL), brine (2×100 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure to afford methyl 2-amino-6-fluorobenzoxazole-4-carboxylate (0.95 g, 87%). 1H NMR and MS consistent. the resulting reaction mixture was heated to reflux for 6 h concentrated under reduced pressure The residue was dissolved in EtOAc (200 mL) washed with H2O (4×100 mL), saturated aqueous ammonium chloride (2×100 mL), brine (2×100 mL) dried over Na2SO4 filtered concentrated under reduced pressure

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of di-(1H-imidazole-1-yl)methanamine (1.05 g, 6.52 mmol) in THF (30 mL) was added methyl-2-amino-5-fluoro-3-hydroxybenzoate (0.96 g, 5.22 mmol) at room temperature and the resulting reaction mixture was heated to reflux for 6 h. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was dissolved in EtOAc (200 mL) and washed with H2O (4×100 mL), saturated aqueous ammonium chloride (2×100 mL), brine (2×100 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure to afford methyl 2-amino-6-fluorobenzoxazole-4-carboxylate (0.95 g, 87%) as a yellow solid. 1H NMR and MS consistent. the resulting reaction mixture was heated to reflux for 6 h concentrated under reduced pressure The residue was dissolved in EtOAc (200 mL) washed with H2O (4×100 mL), saturated aqueous ammonium chloride (2×100 mL), brine (2×100 mL) dried over Na2SO4 filtered concentrated under reduced pressure

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of di-(1H-imidazole-1-yl)methanamine (1.05 g, 6.52 mmol) in THF (30 mL) was added methyl-2-amino-5-fluoro-3-hydroxybenzoate (0.96 g, 5.22 mmol) at room temperature and the resulting reaction mixture was heated to reflux for 6 h. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was dissolved in EtOAc (200 mL) and washed with H2O (4×100 mL), saturated aqueous ammonium chloride (2×100 mL), brine (2×100 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure to afford methyl 2-amino-6-fluorobenzoxazole-4-carboxylate (0.95 g, 87%) as a yellow solid. 1H NMR and MS consistent. the resulting reaction mixture was heated to reflux for 6 h concentrated under reduced pressure The residue was dissolved in EtOAc (200 mL) washed with H2O (4×100 mL), saturated aqueous ammonium chloride (2×100 mL), brine (2×100 mL) dried over Na2SO4 filtered concentrated under reduced pressure

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of methyl 5-fluoro-3-hydroxy-2-nitrobenzoate (1.15 g, 5.34 mmol) in a mixture of CH3OH and glacial acetic acid (3:1, 40 mL) was added 10 wt % palladium on activated charcoal (0.20 g, 17 wt %). The suspension was placed in a Parr hydrogenation apparatus under a H2 atmosphere at 50 psi for 1.5 h. The suspension was filtered through diatomaceous earth eluting with CH2Cl2/CH3OH (9:1, 100 mL). Purification by column chromatography (silica gel, 5 to 100% EtOAc in hexanes) afforded methyl 2-amino-5-fluoro-3-hydroxybenzoate (0.80 g, 83%) as a white solid. 1H NMR and MS consistent. The suspension was filtered through diatomaceous earth eluting with CH2Cl2/CH3OH (9:1, 100 mL) Purification by column chromatography (silica gel, 5 to 100% EtOAc in hexanes)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of methyl 5-fluoro-3-hydroxy-2-nitrobenzoate (1.15 g, 5.34 mmol) in a mixture of CH3OH and glacial acetic acid (3:1, 40 mL) was added 10 wt % palladium on activated charcoal (0.20 g, 17 wt %). The suspension was placed in a Parr hydrogenation apparatus under a H2 atmosphere at 50 psi for 1.5 h. The suspension was filtered through diatomaceous earth eluting with CH2Cl2/CH3OH (9:1, 100 mL). Purification by column chromatography (silica gel, 5 to 100% EtOAc in hexanes) afforded methyl 2-amino-5-fluoro-3-hydroxybenzoate (0.80 g, 83%) as a white solid. 1H NMR and MS consistent. The suspension was filtered through diatomaceous earth eluting with CH2Cl2/CH3OH (9:1, 100 mL) Purification by column chromatography (silica gel, 5 to 100% EtOAc in hexanes)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of di(1H-imidazole-1-yl)methanamine (1.05 g, 6.52 mmol) in THF (30 mL) was added methyl-2-amino-5-fluoro-3-hydroxybenzoate (0.96 g, 5.22 mmol) at room temperature and the resulting reaction mixture was heated to reflux for 6 h. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was dissolved in EtOAc (200 mL) and washed with H2O (4×100 mL), saturated aqueous ammonium chloride (2×100 mL), brine (2×100 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure to afford methyl 2-amino-6-fluorobenzoxazole-4-carboxylate (0.95 g, 87%). 1H NMR and MS consistent. the resulting reaction mixture was heated to reflux for 6 h concentrated under reduced pressure The residue was dissolved in EtOAc (200 mL) washed with H2O (4×100 mL), saturated aqueous ammonium chloride (2×100 mL), brine (2×100 mL) dried over Na2SO4 filtered concentrated under reduced pressure

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of di-(1H-imidazole-1-yl)methanamine (1.05 g, 6.52 mmol) in THF (30 mL) was added methyl-2-amino-5-fluoro-3-hydroxybenzoate (0.96 g, 5.22 mmol) at room temperature and the resulting reaction mixture was heated to reflux for 6 h. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was dissolved in EtOAc (200 mL) and washed with H2O (4×100 mL), saturated aqueous ammonium chloride (2×100 mL), brine (2×100 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure to afford methyl 2-amino-6-fluorobenzoxazole-4-carboxylate (0.95 g, 87%) as a yellow solid. 1H NMR and MS consistent. the resulting reaction mixture was heated to reflux for 6 h concentrated under reduced pressure The residue was dissolved in EtOAc (200 mL) washed with H2O (4×100 mL), saturated aqueous ammonium chloride (2×100 mL), brine (2×100 mL) dried over Na2SO4 filtered concentrated under reduced pressure

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of methyl 5-fluoro-3-hydroxy-2-nitrobenzoate (1.15 g, 5.34 mmol) in a mixture of CH3OH and glacial acetic acid (3:1, 40 mL) was added 10 wt % palladium on activated charcoal (0.20 g, 17 wt %). The suspension was placed in a Parr hydrogenation apparatus under a H2 atmosphere at 50 psi for 1.5 h. The suspension was filtered through diatomaceous earth eluting with CH2Cl2/CH3OH (9:1, 100 mL). Purification by column chromatography (silica gel, 5 to 100% EtOAc in hexanes) afforded methyl 2-amino-5-fluoro-3-hydroxybenzoate (0.80 g, 83%) as a white solid. 1H NMR and MS consistent. The suspension was filtered through diatomaceous earth eluting with CH2Cl2/CH3OH (9:1, 100 mL) Purification by column chromatography (silica gel, 5 to 100% EtOAc in hexanes)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of di(1H-imidazole-1-yl)methanamine (1.05 g, 6.52 mmol) in THF (30 mL) was added methyl-2-amino-5-fluoro-3-hydroxybenzoate (0.96 g, 5.22 mmol) at room temperature and the resulting reaction mixture was heated to reflux for 6 h. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was dissolved in EtOAc (200 mL) and washed with H2O (4×100 mL), saturated aqueous ammonium chloride (2×100 mL), brine (2×100 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure to afford methyl 2-amino-6-fluorobenzoxazole-4-carboxylate (0.95 g, 87%). 1H NMR and MS consistent. the resulting reaction mixture was heated to reflux for 6 h concentrated under reduced pressure The residue was dissolved in EtOAc (200 mL) washed with H2O (4×100 mL), saturated aqueous ammonium chloride (2×100 mL), brine (2×100 mL) dried over Na2SO4 filtered concentrated under reduced pressure

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of di-(1H-imidazole-1-yl)methanamine (1.05 g, 6.52 mmol) in THF (30 mL) was added methyl-2-amino-5-fluoro-3-hydroxybenzoate (0.96 g, 5.22 mmol) at room temperature and the resulting reaction mixture was heated to reflux for 6 h. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was dissolved in EtOAc (200 mL) and washed with H2O (4×100 mL), saturated aqueous ammonium chloride (2×100 mL), brine (2×100 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure to afford methyl 2-amino-6-fluorobenzoxazole-4-carboxylate (0.95 g, 87%) as a yellow solid. 1H NMR and MS consistent. the resulting reaction mixture was heated to reflux for 6 h concentrated under reduced pressure The residue was dissolved in EtOAc (200 mL) washed with H2O (4×100 mL), saturated aqueous ammonium chloride (2×100 mL), brine (2×100 mL) dried over Na2SO4 filtered concentrated under reduced pressure

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of methyl 5-fluoro-3-hydroxy-2-nitrobenzoate (1.15 g, 5.34 mmol) in a mixture of CH3OH and glacial acetic acid (3:1, 40 mL) was added 10 wt % palladium on activated charcoal (0.20 g, 17 wt %). The suspension was placed in a Parr hydrogenation apparatus under a H2 atmosphere at 50 psi for 1.5 h. The suspension was filtered through diatomaceous earth eluting with CH2Cl2/CH3OH (9:1, 100 mL). Purification by column chromatography (silica gel, 5 to 100% EtOAc in hexanes) afforded methyl 2-amino-5-fluoro-3-hydroxybenzoate (0.80 g, 83%) as a white solid. 1H NMR and MS consistent. The suspension was filtered through diatomaceous earth eluting with CH2Cl2/CH3OH (9:1, 100 mL) Purification by column chromatography (silica gel, 5 to 100% EtOAc in hexanes)