Ammonium Chloride → HCID 59598381, compound

Temperature

-78 °C

In a 100 mL round bottom flask under N2, was dissolved 7-methoxy-4-(phenylsulfinyl)quinoline (650 mg, 2.29 mmol) in 10 mL of THF and then the solution was cooled to −78° C. and treated with PhMgBr (3M in Et2O) (1.50 mL, 4.59 mmol). The reaction mixture was then warmed to rt. After 30 min, the mixture was cooled again to −78° C., and solid 4-bromobenzaldehyde (1.27 g, 6.88 mmol) was added. Then, the reaction mixture was warmed to rt. After 2 h the reaction mixture was neutralized with aqueous NH4Cl (sat). The aqueous phase was extracted three times with dichloromethane, and then the organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The crude mixture was purified by MPLC (ISCO dichloromethane:MeOH 100:0 to 90:10) to afford (4-bromophenyl)(7-methoxyquinolin-4-yl)methanol (540 mg, 68.4% yield) as a yellow solid. MS (ESI pos. ion) m/z: 345 (M2H+). Calc'd exact mass for C17H14BrNO2: 343. 1H NMR (400 MHz, CDCl3) 8.83 (d, J=4.42 Hz, 1H), 7.81 (d, J=9.35 Hz, 1H), 7.53 (d, J=4.42 Hz, 1H), 7.44-7.49 (m, 3H), 7.25 (d, J=8.34 Hz, 2H), 7.14 (dd, J=9.28, 2.59 Hz, 1H), 6.43 (s, 1H), 3.93 (s, 3H).

1. temperatureThe reaction mixture was then warmed to rt
2. temperaturethe mixture was cooled again to −78° C.
3. temperatureThen, the reaction mixture was warmed to rt
4. extractionThe aqueous phase was extracted three times with dichloromethane
5. dry with materialthe organic layer was dried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customThe crude mixture was purified by MPLC (ISCO dichloromethane:MeOH 100:0 to 90:10)

ORD record

ord-5e73e9acdbfe4ad3bf6008137fe96627

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08685983B2