(6-Fluoropyridin-3-yl)boronic acid → (S)-3-(6,6-dimethyl-3,6-dihydro-2H-pyran-4-yl)-7-(6-fluoropyridin-3-yl)-5'H-spiro[chromeno[2,3-c]pyridine-5,4'-oxazol]-2'-amine

Participants

Reaction Steps

The titled compound was synthesized by steps analogous to those described in method AA1 above, but using (S)-7-bromo-3-chloro-5′H-spiro[chromeno[2,3-c]pyridine-5,4′-oxazol]-2′-amine (prepared as described in Method BB41), 6-fluoropyridin-3-ylboronic acid and 2-(6,6-dimethyl-3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane. MS m/z=459.0 [M+H]+. Calculated for C26H23FN4O3: 458.18 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.38 (d, J=2.93 Hz, 6 H) 2.53-2.60 (m, 2 H) 3.96 (t, J=5.38 Hz, 2 H) 4.36 (d, J=6.46 Hz, 2 H) 4.55-4.66 (m, 2 H) 6.56 (s, 1 H) 6.98-7.04 (m, 1 H) 7.28 (d, J=8.61 Hz, 1 H) 7.38 (s, 1 H) 7.45-7.53 (m, 1 H) 7.55 (d, J=2.35 Hz, 1 H) 7.87-8.04 (m, 1 H) 8.41 (d, J=2.35 Hz, 1 H) 8.50 (s, 1 H)

Provenance & Evidence