Compound 24
ethyl 8-(bromomethyl)-4H-thieno[3,2-c]thiochromene-2-carboxylate 5,5-dioxide
From: A small molecule interacts with VDAC2 to block mouse BAK-driven apoptosis
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Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
Ethyl 8-methyl-4H-thieno[3,2-c]thiochromene-2-carboxylate 5,5-dioxide (23) (0.61 g, 1.90 mmol) was dissolved in chlorobenzene (10 mL) to that was added n-bromosuccinimide (0.51 g, 2.84 mmol), followed by benzoyl peroxide (0.72 g, 2.08 mmol) portionwise. The reaction was stirred at room temperature for 30 min and than heated to 70 °C for 4 hours. The mixture was diluted with ethyl acetate and washed with sodium sulphate and then brine. The organic layer was dried wih sodium sulphate, the organic was concentrated in vacuo and purified using column chromatography, the product was eluted at 20 % ethyl acetate/cyclohexane, 24 (0.24 g, 0.49 mmol, 26 %) (the product was 80 % pure), yellow solid. 1H-NMR (300 MHz, CDCl3): δ 1.39 (t, J = 7.1 Hz, 3H), 4.39 (q, J = 7.1 Hz, 2H), 4.45 (s, 2H), 4.51 (s, 2H), 7.54 (dd, J = 6.4, 1.7 Hz, 1H), 7.65 (s, 1H), 7.69 (s, 1H), 8.01 (d, J = 8 Hz, 1H). LCMS (ES+), m/z = 402.30 [M+H]+.
