Trifluoroacetic acid → HCID 11472360, compound

Participants

Reaction Conditions

Reaction Steps

4-(1,3-benzodioxol-5-yl)-2-(1-phenylcyclopropyl)-1,3-thiazole (3-1 [synthesized by the method described in Scheme 1], 0.04 g, 0.121 mmol) in methylene chloride (5.0 mL) was cooled to −78° C. and treated with BBr3 (1.0M solution in methylene chloride, 0.60 mL, 0.60 mmol). The reaction stirred 12 h at −78° C. and was subjected directly to reverse phase HPLC (C-8, 5-95% MeOH—H2O w/0.1% TFA) to provide pure 4-(3,4-dihydroxyphenyl)-2-(1-phenylcyclopropyl)-1,3-thiazole (3-2). 1H NMR (300 MHz, CDCl3) δ 7.48 (d, J=7.1 Hz, 2H), 7.39 (m, 3H), 7.51 (d, J=7.6 Hz, 2H), 7.14 (br s, 1H), 7.02 (s, 1H), 6.97 (d, J=7.9 Hz, 1H), 6.72 (d, J=7.9 Hz, 1H), 2.05 (m 2H), 1.70 (m, 2H); MS 309.9 found 310.4 (M+H+) required.

Provenance & Evidence