4-Fluoroaniline → (4-Fluoro-phenyl)-(6,7,8,9-tetrahydro-5H-dipyrido[2,3-b;3',4'-d]pyrrol-4-yl)-amine

Temperature

100 °C

4-Chloro-6,7,8,9-tetrahydro-5H-dipyrido[2,3-b;3′,4′-d]pyrrole (100 mg, 0.48 mmol), 4-fluoroaniline (0.14 mL, 1.44 mmol), Pd(OAc)2 (5 mg, 0.02 mmol), 2-X-Phos (23 mg, 0.05 mmol), and KOH (162 mg, 2.89 mmol) were dissolved in tert-butanol (2.0 mL), and stirred overnight at 100° C. The reaction mixture diluted with EtOAc/H2O, and filtered through an Extrelut column. The column was washed with EtOAc, and the filtrate was concentrated. The crude material was triturated with EtOAc, filtered, washed with EtOAc, and dried under vacuum to provide 5 (35 mg, 26% yield) as a brown solid. LC-MS (M+H=283, obsd.=283).

1. filtrationfiltered through an Extrelut column
2. washThe column was washed with EtOAc
3. concentrationthe filtrate was concentrated
4. customThe crude material was triturated with EtOAc
5. filtrationfiltered
6. washwashed with EtOAc
7. customdried under vacuum

ORD record

ord-de89662f94bc4383838ed8895261140a

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08853391B2