1-(4-fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylic pivalic anhydride

 

1-(4-fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylic pivalic anhydride (10): tan solid,

mp (DSC): onset = 172.4 °C, peak temperature = 173.0 °C;

1H NMR (400 MHz, CD3CN) δ 8.23 (d, J = 7.6 Hz, 1 H), 7.35–7.25 (m, 4 H), 6.36 (d, J = 8.0 Hz, 1 H), 2.02 (s, 3 H), 1.25 (s, 9 H);

13C NMR (100 MHz, CD3CN) 175.9 (1 C), 163.6 (d, 1 C, JCF = 245.4 Hz), 162.9 (1 C ), 161.1 (1 C), 158.2 (1 C), 148.6 (1 C), 135.7 (1 C), 131.0 (d, JCF = 8.7 Hz, 2 C), 117.7 (d, JCF = 23.2 Hz, 2 C), 116.0 (1 C), 107.1 (1 C), 40.4 (1 C), 27.0 (3 C), 22.8 (1 C);

19F NMR (376 MHz, CD3CN) δ -114.2 (m, 1 F);

IR (ATR, cm-1 ) 2966 (w), 2939 (w), 2876 (w), 1789 (vs), 1697 (s), 1682 (vs), 1554 (s), 1509 (vs);

HRMS calcd for C18H18O4NFNa (M+Na+ ) = 354.1112; found 354.1113, δ = 0.3 ppm.

//////////////https://pubs.acs.org/doi/suppl/10.1021/acs.oprd.8b00441

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