Benzo(B)Thiophene → HCID 58591561, compound

Temperature

-78 °C

To a cooled (−78° C.) solution of benzothiophene (74.5 mmol) in anhydrous THF (100 mL) was added slowly n-BuLi (82 mmol, 1.6 M in hexanes). The mixture was stirred at −78° C. for 1 hr. β-Dimethylaminoethyl bromide hydrobromide (41 mmol) was added at −78° C. and the temperature was allowed to reach 0° C. over 5 hours. The mixture was quenched in sat. NH4Cl, the pH of the aqueous layer was adjusted to 7-8 with sat. NaHCO3, and the mixture was extracted with EtOAc (4×). The combined organic layers were concentrated and extracted with 1N HCl (3×). The combined HCl layers were made basic with sat. NaHCO3, extracted with EtOAc (4×), and the combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated in vacuo to afford Compound 1a (2-Benzo[b]thiophen-2-yl-ethyl)-dimethyl-amine (4.96 g, 65%) as a tan solid; MS (MH+)=206.

1. waitto reach 0° C. over 5 hours
2. customThe mixture was quenched in sat. NH4Cl
3. extractionthe mixture was extracted with EtOAc (4×)
4. concentrationThe combined organic layers were concentrated
5. extractionextracted with 1N HCl (3×)
6. extractionextracted with EtOAc (4×)
7. washthe combined organic layers were washed with brine
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. concentrationconcentrated in vacuo

ORD record

ord-6d3d4bee1ea2456198465e9722e4f461

Source dataset

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07393865B2