Dimethylformamide → HCID 51051282, compound

Temperature

-50 °C

7-Bromo-2-phenyl-quinoline (40.0 g, 0.141 mol) was added to a 1000 mL three-neck round bottom flask (rbf). The flask was degassed and filled with N2. THF (400 mL) was added. The solid dissolved. The flask was kept in a cooling bath (at −62° C.). The off-white solid crashed out at low temperature. 1.4 M of sec-butyllithium in cyclohexane (125.7 mL, 0.176 mol) was added within 15 min, and the internal temperature was kept at around −50° C. After addition was complete, the reaction was stirred at −50° C. (internal temperature) for 5 min. DMF (13.6 mL, 0.176 mol) was added within 10 min and the internal temperature was always kept at around −50° C. and the cooling bath was kept at around at −62° C. After 35 min, the reaction was quenched by NH4Cl/water (200 mL), and EtOAc (200 mL) was added. The organic layer was washed with water (300 mL×2) and brine (150 mL), dried over MgSO4, filtered and concentrated in vacuo. After evaporating to almost dryness, EtOAc (200 mL) was added and heated in a 70° C. oil bath to dissolve the solid. Half of the aminodiphenylmethane (26.2 mL, 0.148 mol) was added and the reaction was stirred at 58° C. (internal temperature) for 5 min. The reaction was seeded and the solid came out of solution slowly. After 5 min, the remaining aminodiphenylmethane was added within 3 min. The oil bath temperature was kept at 70° C., the internal temperature increased to 67° C. After 10 min, the reaction mixture was cooled in an ice bath. The off-white solid was collected by vacuum filtration and dried in vacuo at 40-60° C. for 2 hours. The title compound was isolated as an off-white solid (37.42 g, 67% yield).

1. customThe flask was degassed
2. additionfilled with N2
3. additionTHF (400 mL) was added
4. dissolutionThe solid dissolved
5. customThe flask was kept in a cooling bath
6. custom(at −62° C.)
7. customwas kept at around −50° C
8. additionAfter addition
9. customwas always kept at around −50° C.
10. customwas kept at around at −62° C
11. waitAfter 35 min
12. customthe reaction was quenched by NH4Cl/water (200 mL), and EtOAc (200 mL)
13. additionwas added
14. washThe organic layer was washed with water (300 mL×2) and brine (150 mL)
15. dry with materialdried over MgSO4
16. filtrationfiltered
17. concentrationconcentrated in vacuo
18. customAfter evaporating to almost dryness, EtOAc (200 mL)
19. additionwas added
20. temperatureheated in a 70° C. oil bath
21. dissolutionto dissolve the solid
22. stirringthe reaction was stirred at 58° C. (internal temperature) for 5 min
23. waitAfter 5 min
24. customwas kept at 70° C.
25. temperaturethe internal temperature increased to 67° C
26. waitAfter 10 min
27. temperaturethe reaction mixture was cooled in an ice bath
28. filtrationThe off-white solid was collected by vacuum filtration
29. customdried in vacuo at 40-60° C. for 2 hours

ORD record

ord-4d06bfd03db94779875f6a812a4573f1

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08513415B2