Sulfuric Acid → HCID 86723392, compound

Participants

Reaction Steps

Following the procedure of Example 12, 6-(diethoxymethyl)-3-fluoro-6′-(trifluoromethyl)-N-trityl-[2,3′-bipyridin]-4-amine (1203 mg, 2 mmol), conc H2SO4 (0.5 mL), CH3CN (25 mL) and H2O (25 mL) gave 4-amino-3-fluoro-6′-(trifluoromethyl)-[2,3′-bipyridine]-6-carbaldehyde (248 mg, 0.861 mmol, 43.0%) as a white solid: mp 166-167° C.; 1H NMR (400 MHz, CDCl3) δ 9.97 (s, 1H), 9.35 (s, 1H), 8.54 (d, J=8.2 Hz, 1H), 7.84 (d, J=8.2 Hz, 1H), 7.40 (d, J=6.5 Hz, 1H), 4.67 (s, 2H); 13C NMR (101 MHz, CDCl3) δ 192.35, 149.96 (d, J=8.9 Hz), 149.50 (d, J=5.2 Hz), 149.03 (d, J=260.1 Hz), 145.2, 143.03 (d, J=12.4 Hz), 140.95, 137.48 (d, J=5.3 Hz), 133.55, 122.83, 120.25 (d, J=2.7 Hz), 108.70 (d, J=4.3 Hz); 19F NMR (376 MHz, CDCl3) δ −67.98, −142.26; HRMS-ESI (m/z) [M+H]+ calcd for C12H7F4N3O, 285.0525. found, 285.0525.

Provenance & Evidence