Dichloromethane → HCID 86730378, compound

Participants

Reaction Conditions

Reaction Steps

2-Amino-5-fluoropyridine (0.048 g, 0.427 mmol), 3-bromoacetylpyridine hydrobromide (0.10 g, 0.356 mmol) and chloroform (3.56 mL) were added to a microwave vial. To the resulting solution were added a solution of TiCl4 in dichloromethane (1.0 M, 0.267 mL, 0.267 mmol) and triethylamine (0.030 mL, 0.214 mmol). The reaction was then heated in a microwave at 110° C. for 30 minutes. The resulting mixture was poured into aqueous sodium hydroxide solution (1.0 N) and extracted with ethyl acetate. The organic extracts were combined, dried over MgSO4, filtered and concentrated under reduced pressure. Purification by flash chromatography on silica gel (50% to 100% ethyl acetate in hexanes) provided the title compound: LCMS m/z 214.09 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 9.13 (d, J=1.7 Hz, 1H), 8.59-8.58 (m, 1H), 8.29-8.28 (m, 1H), 8.10 (t, J=2.9, 2.9 Hz, 1H), 7.95 (s, 1H), 7.63 (dd, J=9.9, 5.1 Hz, 1H), 7.40 (dd, J=7.9, 5.0 Hz, 1H), 7.18-7.14 (m, 1H).

Provenance & Evidence