Cesium carbonate → 5-(2,4-dichloro-phenyl)-3-hydroxy-1-methyl-1H-pyridin-2-one

Beteiligte Stoffe

Reaktionsschritte

To a suspension of 0.045 (0.15 mmol) 3-benzyloxy-5-bromo-1-methyl-1H-pyridin-2-one, 0.44 g (0.23 mmol) 2,6-dichlorophenylboronic acid, and 0.006 g (0.008 mmol) dichloro 1,1′-bis(diphenylphosphino)ferrocene palladium (II) dichloromethane adduct in 2 mL THF was added 1 mL 1 M aq Cs2CO3. The resulting mixture was microwaved to 160° C. for 10 min. After cooling, the organic phase was separated and concentrated and the resulting residue was re-dissolved in MeOH. 0.02 mg (0.019 mmol) 10% Pd/C was added and the resulting suspension was stirred under 1 atm hydrogen gas overnight. The reaction mixture was filtered and concentrated. Purification by automated mass-guided HPLC afforded 0.045 g (11%) 5-(2,4-dichloro-phenyl)-3-hydroxy-1-methyl-1H-pyridin-2-one. 1H NMR (499 MHz, DMSO-d6): δ 9.29 (s, 1 H); 7.71 (d, J=2.13 Hz, 1 H); 7.48 (dd, J=8.32, 2.19 Hz, 1 H); 7.43 (d, J=8.30 Hz, 1 H); 7.34 (d, J=2.35 Hz, 1 H); 6.82 (d, J=2.35 Hz, 1 H); 3.53 (s, 3 H). High resolution mass spec (FT/ICR) calc (M+H)+=270.0084 found 270.0083.

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