Tri(butyl)vinyltin → 7-methoxy-2-phenyl-6-vinylquinolin-4(1H)-one

Temperatur

100 °C

To a solution of 6-bromo-7-methoxy-2-phenylquinolin-4(1H)-one (1.0 g, 3.03 mmol) in DMSO (35 mL) was added tri(n-butyl)vinyltin (1.06 mL, 3.63 mmol) and finally tetrakis(triphenylphosphine)palladium (88 mg, 0.076 mmol). The mixture was then degassed using a freeze/pump/thaw cycle (2×). The mixture was then heated to 100° C. in a sealed tube for 22 h. At this time, LC-MS revealed complete consumption of the bromoquinoline). The reaction mixture was then poured into a mixture of water (200 mL) and EtOAc (200 mL) which caused solid to crash out. The solid was filtered off, washed with CH3CN, EtOAc, DCM, and then hexanes to give 7-methoxy-2-phenyl-6-vinylquinolin-4(1H)-one as a light greenish solid (670 mg, 80%). 1H NMR (400 MHz, DMSO-d6) ppm: 11.58 (s, 1H), 8.16 (s, 1H), 7.83 (m, 2H), 7.58 (m, 3H), 7.25 (s, 1H), 6.99 (dd, J=11 Hz, 17.5 Hz, 1H), 6.28 (s, 1H), 5.85 (d, J=17.5 Hz, 1H), 5.31 (d, J=11 Hz, 1H), 3.92 (s, 3H). LRMS (CI, [M+H]) Calc'd=278.1. found=278.2.

1. customThe mixture was then degassed
2. customconsumption of the bromoquinoline)
3. additionThe reaction mixture was then poured into a mixture of water (200 mL) and EtOAc (200 mL) which
4. filtrationThe solid was filtered off
5. washwashed with CH3CN, EtOAc, DCM

ORD-Eintrag

ord-55d57672ceac41509d0723169341317a

Quelldatensatz

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07879797B2