1-Methylpiperazine → 3-Methoxy-4-[(trimethylsilyl)ethynyl]phenyl-4-methylpiperazine

A solution of [(4-bromo-2-methoxyphenyl)ethynyl](trimethyl)silane (1.426 g, 5.035 mmol) in dry THF (25 mL) was degassed and backfilled with argon for three times. Pd2(dba)3 (230.5 mg, 0.252 mmol) and 2-dicyclohexylphosphino-2-(N,N′-dimethylamino)biphenyl (79.3 mg, 0.201 mmol) were added under argon atmosphere and the mixture was degassed and backfilled with argon for three times. Then 1 M LiHMDS in THF (12.1 mL, 12.084 mmol) and N-methylpiperazine (1.34 mL, 1.21 g, 12.083 mmol) were added by a syringe and the mixture was degassed and backfilled with Argon for three times. The reaction mixture was heated to reflux for 1 h. After cooling to room temperature the reaction mixture was filtered on a pad of celite washing with THF (200 mL). The filtrate was evaporated under vacuum and the black oil so obtained was purified by chromatography on silica gel (DCM/MeOH 9/1) to afford the title compound as a brownish solid (1.042 g, 68.4%).

1. customthe mixture was degassed
2. customthe mixture was degassed
3. temperatureThe reaction mixture was heated
4. temperatureto reflux for 1 h
5. filtrationwas filtered on a pad of celite
6. washwashing with THF (200 mL)
7. customThe filtrate was evaporated under vacuum
8. customthe black oil so obtained
9. customwas purified by chromatography on silica gel (DCM/MeOH 9/1)

ORD-Eintrag

ord-2647c7aa74384512ad91b54f599d80a0

Quelldatensatz

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08912200B2