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With hydrazine hydrate; In ethanol; at 70.0℃; for 16.0h;
3-Fluoro-isonicotinonitrile (0.50 g, 4.10 mmol) was dissolved in ethanol (8 mL) and treated with hydrazine hydrate (0.31 g, 6.1 mmol). After stirring at 70 C for 16 h, the mixture was cooled to RT and concentrated in vacuo and dried to yield the title compound (0.66 g, 100% of theory). LC-MS (Method 2B): Rt = 0.51 min, MS (ESIPos): m/z = 135 [M+H]+
0.66 g
With hydrazine hydrate; In ethanol; at 70.0℃; for 16.0h;
Example 15A 1H-Pyrazolo[3,4-c]pyridin-3-amine 3-Fluoro-isonicotinonitrile (0.50 g, 4.10 mmol) was dissolved in ethanol (8 mL) and treated with hydrazine hydrate (0.31 g, 6.1 mmol). After stirring at 70 C. for 16 h, the mixture was cooled to RT and concentrated in vacuo and dried to yield the title compound (0.66 g, 100% of theory). LC-MS (Method 2B): Rt=0.51 min, MS (ESIPos): m/z=135 [M+H]+
tert-butyl (2S)-2-[(4-cyanopyridin-3-yl)oxy]methyl}azetidine-1-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
75.96%
To a stirred mixture of tert-butyl (2S)-2-(hydroxymethyl) azetidine-1-carboxylate (1533 mg, 8.19 mmol, 1.00 equiv) and NaH (60% in oil, 491 mg, 12.29 mmol, 1.50 equiv) in THF (14.00 mL) in portions at 0 degrees C under nitrogen atmosphere. The resulting mixture was stirred for 30 min at 0 degrees C under nitrogen atmosphere. To the above mixture was added 3-fluoropyridine-4-carbonitrile (1000 mg, 8.19 mmol, 1.00 equiv) in portions over 1 min at 0 degrees C. The resulting mixture was stirred for overnight at room temperature under nitrogen atmosphere. Desired product could be detected by LCMS. The resulting mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography, eluted with PE / EA (1:1) to afford tert- butyl (2S)-2-[(4-cyanopyridin-3-yl)oxy]methyl}azetidine-1-carboxylate (1800 mg, 75.96%) as a white solid. LC-MS: (M+H)+ found 290.15
75.96%
To a stirred mixture of tert-butyl (2S)-2-(hydroxymethyl) azetidine-1-carboxylate (1533 mg, 8.19 mmol, 1.00 equiv) and NaH (60% in oil, 491 mg, 12.29 mmol, 1.50 equiv) in THF (14.00 mL) in portions at 0 degrees C under nitrogen atmosphere. The resulting mixture was stirred for 30 min at 0 degrees C under nitrogen atmosphere. To the above mixture was added 3-fluoropyridine-4-carbonitrile (1000 mg, 8.19 mmol, 1.00 equiv) in portions over 1 min at 0 degrees C. The resulting mixture was stirred for overnight at room temperature under nitrogen atmosphere. Desired product could be detected by LCMS. The resulting mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography, eluted with PE / EA (1:1) to afford tert- butyl (2S)-2-[(4-cyanopyridin-3-yl)oxy]methyl}azetidine-1-carboxylate (1800 mg, 75.96%) as a white solid. LC-MS: (M+H)+ found 290.15
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