Potassium Carbonate → HCID 23653815, Verbindung

Temperatur

110 °C

A mixture of 3-bromo-2-methoxy-5-methyl-7-(trifluoroacetyl)-6,7,8,9-tetrahydro -5H-pyrido[2,3-d]azepine (220 mg, 599 μmol), Bu3SnCH═CH2 (523 μl, 1.79 mmol), Pd(PPh3)4 (50 mg), and toluene (10 ml) was heated in a sealed tube at 110° C. for 16 h. The solvent was evaporated and the resulting residue was purified by column chromatography to render 165 mg (88%) of 2-methoxy-5-methyl-7-(trifluoroacetyl)-3-vinyl-6,7,8,9-tetrahydro-5H-pyrido[2,3-d]azepine. A mixture of 2-methoxy-5-methyl-7-(trifluoroacetyl)-3-vinyl-6,7,8,9-tetrahydro-5H-pyrido[2,3-d]azepine (32 mg, 102 μmol), K2CO3 (40 mg), MeOH (5 ml) and H2O (1 ml) was heated to reflux for 10 min. The reaction mixture was concentrated in vacuo and the resulting residue was purified by column chromatography to yield 17.0 mg (77%) of 2-methoxy-5-methyl-3-vinyl-6,7,8,9-tetrahydro-5H-pyrido[2,3-d]azepine. 1H-NMR (CDCl3) δ 7.58 (s, 1H), 6.92 (dd, 1H), 5.86 (d, 1H), 5.40 (d, 1H), 4.02 (s, 3H), 3.60-3.40 (m, 4H), 3.31 (m, 1H), 3.18 (dd, 1H), 3.00 (m, 1H), 1.52 (d, 3H) ppm.

1. customThe solvent was evaporated
2. customthe resulting residue was purified by column chromatography
3. temperaturewas heated
4. temperatureto reflux for 10 min
5. concentrationThe reaction mixture was concentrated in vacuo
6. customthe resulting residue was purified by column chromatography

ORD-Eintrag

ord-2c04d402e6e44850ac4d80f992ca9724

Quelldatensatz

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07897595B2