Tributyltin Chloride → 4-Pyrrol-1-yl-2-tributylstannanyl-pyridine

Temperature

0 °C

In a round-bottomed flask, 2-bromo-4-(1H-pyrrol-1-yl)pyridine (0.20 g, 0.90 mmol) was dissolved in THF (6 mL). The light yellow solution was cooled to 0° C. and isopropylmagnesium chloride lithium chloride complex (1.3 M solution in THF, 0.78 mL, 1.0 mmol) was added dropwise. The reaction mixture was stirred at 0° C. for 40 min and at room temperature for 2 h. The reaction mixture was cooled to 0° C. and tributyltin chloride (0.28 mL, 1.03 mmol) was slowly added. After the addition was complete, the ice bath was removed and the reaction mixture was stirred at room temperature for 1.5 h. The reaction mixture was quenched with saturated NH4Cl solution and then extracted with 50 mL EtOAc (2×). The combined organic layers were washed with ˜5 mL water and ˜5 mL brine then dried over sodium sulfate, filtered and concentrated to provide 4-pyrrol-1-yl-2-tributylstannanyl-pyridine as a light brown oil which was used without further purification.

1. temperatureThe reaction mixture was cooled to 0° C.
2. additionAfter the addition
3. customthe ice bath was removed
4. stirringthe reaction mixture was stirred at room temperature for 1.5 h
5. customThe reaction mixture was quenched with saturated NH4Cl solution
6. extractionextracted with 50 mL EtOAc (2×)
7. washThe combined organic layers were washed with ˜5 mL water and ˜5 mL brine
8. dry with materialthen dried over sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated

ORD record

ord-f3988b0fae7747529e96054a94e3618b

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08518945B2