6-fluoroimidazo[1,5-a]pyridine synthesis

3synthesis methods

Product Name:6-fluoroimidazo[1,5-a]pyridine
CAS Number:1426421-17-1
Molecular formula:C7H5FN2
Molecular Weight:136.13

Formamide, N-[(5-fluoro-2-pyridinyl)methyl]-

1426421-16-0
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Yield:1426421-17-1 517 mg

Reaction Conditions:

with trichlorophosphate in toluene at 100; for 4 h;

Steps:

32.3 Step 36-Fluoro-imidazo[l ,5-a]pyridine

Step 36-Fluoro-imidazo[l ,5-a]pyridineIn a round-bottomed flask, N-(5-fluoro-pyridin-2-ylmethyl)-formamide (612 mg, 3.97 mmol) was dissolved in toluene (16 ml) and phosphorus oxychloride (0.68 ml, 7.3 mmol) was added. The reaction mixture was stirred at 100°C in an oil bath for 4 h then cooled to 0°C and carefully quenched with ice. Aqueous 25% ammonium hydroxide ws added until pH=~9. The mixture was diluted with water and extracted with dichloromethane (3x). The organic layers were combined, dried over sodium sulfate, filtered and concentrated to give 517 mg (96%) of 6- fluoro-imidazo[l ,5-a]pyridine as a light brown oil. ^lU NMR (CDC1₃, 300 MHz): ? (ppm) 8.16 (s, 1H), 7.84 - 7.94 (m, 1H), 7.50 (s, 1H), 7.46 (dd, J=9.8, 5.3 Hz, 1H), 6.69 (ddd, J=9.8, 7.7, 2.1 Hz, 1H).

References:

WO2013/30138,2013,A1 Location in patent:Page/Page column 109

327056-62-2 Synthesis

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References

561297-96-9 Synthesis

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References