Boron Trichloride → HCID 136372776, compound

Participants

Reaction Steps

Boron trichloride (1 M in CH2Cl2, 3 mL was added to a solution of ethyl 3-(4-(5-(3-cyano-4-isopropyloxyphenyl)-1,3,4-thiadiazol-3-yl)-3-methylphenyl)propanoate (0.6 mmol, from Step C) in methylene chloride (40 mL) at 0° C. The reaction mixture was allowed to warm to rt over 4 h and then was stirred at rt for 16 h. The reaction mixture was diluted with methylene chloride (50 mL) and washed with water (50 mL). The organics were dried over magnesium sulfate, filtered and concentrated in vacuo. Silica gel chromatography eluting with EtOAc yielded 0.12 g of the title compound. 1H NMR (500 MHZ, CDCl3) δ 1H NMR (500 MHZ, CDCl3) δ 8.17 (s, 1H), 8.13 (s, 1H), 7.68 (s, 1H), 7.24 (s, 1H), 7.20-7.24 (m, 2H), 4.14-4.23 (m, 2H), 2.98-3.08 (m, 2H), 2.68-2.78 (m, 2H), 2.64 (s, 3H), 1.30 (t, J=7.1, 3H); ESI-MS (m/z) 394.2; HPLC A: 2.71 min.

Provenance & Evidence