Dimethylamine → HCID 71729794, compound

Temperature

85 °C

An oven-dried sealed tube (0.5-2 mL) was equipped with a stir bar and charged with the precatalyst (0.003 g, 0.004 mmol). The tube was closed with a septum, then evacuated and refilled with nitrogen three times through a needle. LHMDS (0.3 mL of a 1.0 M solution in THF, 0.32 mmol) and compound 6b (0.038 g, 0.16 mmol) in THF (0.3 mL) were added via syringe. Finally, dimethylamine (0.3 mL of a 2.0 M solution in THF, 0.24 mmol) in THF (0.3 mL) was added at rt via syringe. The resulting solution was heated at 85° C. in an oil bath and stirred for 3 h. The consumption of the starting material was monitored by TLC. Once the reaction was complete, the mixture was cooled rt, diluted with sat'd aq ammonium chloride solution (10 mL), and then extracted with AcOEt (3×12 mL). The combined organic layers were dried over Na2SO4, gravity filtered, and concentrated in vacuo. The crude product was purified by flash chromatography (n-hexane/AcOEt 9.25:0.7) and the pure product was isolated as a yellow solid (70% yield).

1. customAn oven-dried sealed tube (0.5-2 mL)
2. customwas equipped with a stir bar
3. additioncharged with the precatalyst (0.003 g, 0.004 mmol)
4. customThe tube was closed with a septum
5. customevacuated
6. additionrefilled with nitrogen three times through a needle
7. customThe consumption of the starting material
8. temperaturethe mixture was cooled rt
9. additiondiluted with sat'd aq ammonium chloride solution (10 mL)
10. extractionextracted with AcOEt (3×12 mL)
11. dry with materialThe combined organic layers were dried over Na2SO4, gravity
12. filtrationfiltered
13. concentrationconcentrated in vacuo
14. customThe crude product was purified by flash chromatography (n-hexane/AcOEt 9.25:0.7)

ORD record

ord-f52989d4132041179ebf2239cc55727c

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09133234B2