Benzoyl chloride → HCID 131724857, Verbindung

Temperatur

125 °C

Amide 5 was prepared from commercial reagents, benzoyl chloride and 3-amino-2,6-dichloropyridine in DCM in high yield. The desired product 4g was prepared by dissolving amide 5 (4.45 g, 16.7 mmol) in DMA (35 mL) and adding sodium carbonate (1.8 g, 16.7 mmol) and palladium acetate (400 mg, catalytic amt.). The reaction mixture was heated to 125° C. for several hours until the stating material was no longer present by TLC. The reaction was then cooled down to room temperature and concentrated in vacuo and the crude residue was suspended in boiling EtOAc (100 mL) and filtered through a plug of celite. The filtrate was concentrated and the solid that precipitated out was filtered off and determined to be compound 4g (520 mg, 13% yield). Mp=285-295 (dec.) ° C.; 1H NMR (d6-DMSO) δ 11.92 (bs, 1H), 8.62 (d, 1H), 8.32 (d, 1H), 7.95 (t, 1H), 7.77 (m, 2H), 7.62 (d, 1H). Anal Calcd. for C12H7ClN2O: C, 62.49; H, 3.06; N, 12.15. Found: C, 61.40; H, 3.19; N, 11.77.

1. customThe desired product 4g was prepared
2. temperatureThe reaction was then cooled down to room temperature
3. concentrationconcentrated in vacuo
4. filtrationfiltered through a plug of celite
5. concentrationThe filtrate was concentrated
6. customthe solid that precipitated out
7. filtrationwas filtered off

ORD-Eintrag

ord-c1c0117d5a3647f49a6c4ec290315969

Quelldatensatz

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07915280B2