HCID 86624700, compound → HCID 25107426, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 100 mg (0.32 mmol) 2-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamino]-thiazole-5-carbaldehyde in DMPU (1 ml) and tetrahydrofurane (2 ml) was added slowly 0.67 ml (1.27 mmol) 1.9 M phenyl lithium solution in diethyl ether at −72° C. under nitrogen. The reaction was warmed to 0° C. over 40 minutes. The solvent was evaporated under reduced pressure. The residue was partitioned between in ethyl acetate and 1N aqueous NaOH solution. The aqueous layer was extracted once with ethyl acetate. The combined organic layers were washed twice with water, dried over sodium sulphate, filtered and the solvent was evaporated under reduced pressure. The residue was purified on silica gel with methylene chloride/methanol 9/1 yielding 39 mg (22%) {2-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamino]-thiazol-5-yl}-phenyl-methanol as a yellow oil. MS ISP (m/e): 393.0 (100) (M+H)+. 1H NMR (CDCl3, 250 MHz): δ (ppm)=7.56 (s, 1H), 7.47-6.84 (m, 11H), 5.99 (s, 1H), 3.79 (s, 3H), 2.28 (s, 3H).

Provenance & Evidence