Reaktion #70560

Reaktionsgleichung

1-benzyl-2-phenyl-1H-imidazole

3-(1-benzyl-1H-imidazol-2-yl)pyridine

3-cyanopyridine

FPBA

3-flourobenzene boronic acid

→

title compound

2-(3-fluorophenyl)-5-(2-(pyridin-3-yl )-1H-imidazol-5-yl)pyrimidine

Lösungsmittel

dichloromethane methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeprepared

Vorschrift

The title compound was prepared by the method described in Example 1, except that (i) commercially available 3-flourobenzene boronic acid was used instead of benzeneboronic acid in Step A, and (ii) 3-(1-benzyl-1H-imidazol-2-yl)pyridine (prepared according to the method described in Example 8, Step A, except that commercially available 3-cyanopyridine was used instead of 3-fluorobenzonitrile) was used in place of the 1-benzyl-2-phenyl-1H-imidazole in Step C; Rf 0.35 with 95:5 v/v dichloromethane-methanol; melting point 309° C; 1H-NMR (400 MHz; DMSO-d6) δ 9.40 (s, 2H), 9.27 (d,1H), 8.64 (dd, 1H), 8.40 (dt, 1H), 8.31 (dd, 1H), 8.23 (bs, 1H), 8.18-8.13 (m, 1H), 7.66-7.55 (m, 3H), 7.42 (dt, 1H); MS (ESI+) m/z 318.0 (M+1); H-PGDS FPBA IC50: 0.156 μM; H-PGDS inhibitor EIA IC50: 0.041 μM.

Quelle