Tributyltin Chloride → (6-Fluoro-1-tributylstannanyl-imidazo[1,5-a]pyridin-3-yl)-methanol

In a round-bottomed flask, (6-fluoro-1-iodo-imidazo[1,5-a]pyridin-3-yl)-methanol (156 mg, 0.53 mmol) was dissolved in THF (4 ml). Sodium hydride (60% dispersion in mineral oil, 26 mg, 0.65 mmol) was added and the reaction mixture was stirred at room temperature for 10 min. The reaction mixture was cooled to −16° C. (NaCl/ice bath) and isopropylmagnesium chloride (2.0 M in THF, 0.32 ml, 0.64 mmol) was added dropwise. The reaction was stirred at −16° C. for 25 min then tributylchlorostannane (0.17 ml, 0.63 mmol) was slowly added. The reaction mixture was allowed to warm to room temperature and stirred for 1.5 h then quenched with saturated aqueous NH4Cl and extracted with EtOAc (2×). The combined organic layers were washed with water and brine then dried over sodium sulfate, filtered and concentrated to afford (6-Fluoro-1-tributylstannanyl-imidazo[1,5-a]pyridin-3-yl)-methanol as a brown semisolid which was used without further purification.

1. additionwas added dropwise
2. stirringThe reaction was stirred at −16° C. for 25 min
3. temperatureto warm to room temperature
4. stirringstirred for 1.5 h
5. customthen quenched with saturated aqueous NH4Cl
6. extractionextracted with EtOAc (2×)
7. washThe combined organic layers were washed with water and brine
8. dry with materialthen dried over sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated

ORD record

ord-92d581dfacdb4b7591c1827d0c7f5e9f

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08658646B2