N-pyridin-3-ylpyridin-3-amine → N-(1-(2-bromophenyl)ethyl)-N-(pyridin-3-yl)pyridin-3-amine

To a cooled solution (−78° C.) of N-pyridin-3-ylpyridin-3-amine (0.886 g, 5.23 mmol) in dry tetrahydrofuran (20 mL) was added LDA (3.8 mL of a 1.5 M solution, 5.75 mmol) to form a light yellow suspension. After stirring for 30 min, 1-bromo-2-(1-bromoethyl)benzene (3-1) (1.38 g, 5.23 mmol) was added in one portion. The reaction was stirred for 30 min at −78° C. then allowed to warmn to 0° C. and quenched with NH4Cl sat. solution (6 mL). The mixture was diluted with water and extracted with THF (2×20 mL), washed with brine and the organic layer was dried over Na2SO4. The solution was then filtered, concentrated, and dried under vacuum to give crude N-(1-(2-bromophenyl)ethyl)-N-(pyridin-3-yl)pyridin-3-amine (3-2) as a light brown solid (4.40 g): Analytical LCMS: (214 nm), 2.043 min. m/e (m+1): 356.1

1. customto form a light yellow suspension
2. stirringThe reaction was stirred for 30 min at −78° C.
3. customto warmn to 0° C.
4. customquenched with NH4Cl sat. solution (6 mL)
5. additionThe mixture was diluted with water
6. extractionextracted with THF (2×20 mL)
7. washwashed with brine
8. dry with materialthe organic layer was dried over Na2SO4
9. filtrationThe solution was then filtered
10. concentrationconcentrated
11. customdried under vacuum

ORD-Eintrag

ord-be3737b2942b43e28351a99aa0d767a0

Quelldatensatz

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08067607B2