1-Methylimidazole → 1-Methyl-5-(tri-n-butylstannyl)imidazole

Butyllithium (3.75 mL, 9.40 mmol) and TMEDA (2.24 mL, 14.85 mmol) were stirred at −20° C. in hexanes (7 mL) in an ethanol/dry ice/water bath for 30 minutes. 1-Methylimidazole (0.5 mL, 6.27 mmol) was added and the mixture stirred at room temperature for 1 h. After cooling to −20° C., Bu3SnCl (1.70 mL, 15.67 mmol) was added dropwise. The reaction stirred for 15 minutes at −20° C. then at room temperature overnight before being quenched with 1:1 EtOAc/water (20 mL). The layers were separated and the aqueous layer extracted with EtOAc (3×). The combined organics were washed with water, dried over Na2SO4, concentrated, and chromatographed (4:96 MeOH/EtOAc) to give 1-methyl-5-tributylstannanyl-1H-imidazole (0.486 g).

1. temperatureAfter cooling to −20° C.
2. stirringThe reaction stirred for 15 minutes at −20° C.
3. customat room temperature overnight before being quenched with 1:1 EtOAc/water (20 mL)
4. customThe layers were separated
5. extractionthe aqueous layer extracted with EtOAc (3×)
6. washThe combined organics were washed with water
7. dry with materialdried over Na2SO4
8. concentrationconcentrated
9. customchromatographed (4:96 MeOH/EtOAc)

ORD record

ord-1d00048b1e3c427aa7636777089a06f2

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07514458B2