Diisopropylamine → 5H-benzo[b]pyrido[4,3-f]azepin-6(11H)-one

Temperature

-78 °C

To a solution of diisopropylamine (7.61 mL, 53.89 mmol) and tetramethylethylenediamine (8.13 mL, 53.89 mmol) in THF (50 mL) was added n-butyllithium (1.6 M, 34.2 mL, 54.77 mmol) at −78° C. The mixture was stirred at −78° C. for 30 min., then 0° C. for 10 min. This solution was transferred into a solution of N,N-dimethyl-2-((4-methylpyridin-3-yl)amino)benzamide in THF (100 mL) at 0° C. The resulting solution was stirred overnight and quenched by adding saturated ammonium chloride solution (20 mL). The solvent was then removed under reduced pressure and the residue dissolved in dichloromethane (100 mL), washed with water (100 mL), dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by flash chromatography (SiO2, 50% hexane in ethyl acetate) to afford the pure desired product, 5H-benzo[b]pyrido[4,3-f]azepin-6(11H)-one (2.2 g) as a yellow solid. 400 MHz 1H NMR (DMSO-d6) δ 9.68 1H), 8.53 (s, 1H), 8.27 (d, J=4.4 Hz, 1H), 7.79 (m, 1H), 7.53-7.49 (m, 1H), 7.38-6.89 (m, 2H), 6.93-6.89 (m, 1H), 3.78 (s, 2H); LCMS (M+H)=211.

1. wait0° C. for 10 min
2. stirringThe resulting solution was stirred overnight
3. customquenched
4. additionby adding saturated ammonium chloride solution (20 mL)
5. customThe solvent was then removed under reduced pressure
6. dissolutionthe residue dissolved in dichloromethane (100 mL)
7. washwashed with water (100 mL)
8. dry with materialdried over sodium sulfate
9. concentrationconcentrated under reduced pressure
10. customThe crude product was purified by flash chromatography (SiO2, 50% hexane in ethyl acetate)

ORD record

ord-6828d00db16d468ea0df8e65a41be132

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08349827B2