Stannous chloride dihydrate → HCID 16045450, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-chloro-N-isopropyl-5-nitro-N-[4-(1,1,1-trifluoro-2-hydroxypropan-2-yl)phenyl]benzenesulfonamide (11) (704 mg, 1.50 mmol, 1.0 equiv) in EtOH (40 mL) was treated with SnCl2.2H2O (1.70 g, 7.50 mmol, 5.0 equiv). After stirring at 75° C. for 2 h, the reaction mixture was concentrated under reduced pressure, diluted (EtOAc) and washed (3×1 M aqueous NaOH and 1×brine). The organics were dried (Na2SO4) and concentrated under reduced pressure. Flash chromatography of the residue (SiO2, 30-40% EtOAc/Hexane, gradient elution) gave the product as a white foam. 1H NMR (DMSO-d6, 500 MHz) δ 7.59 (d, J=8.6 Hz, 2H), 7.28 (d, J=8.6 Hz, 1H), 7.12 (d, J=8.6 Hz, 2H), 7.08 (d, J=2.8 Hz, 1H), 6.73 (dd, J=2.8, 8.6 Hz, 1H), 6.65 (s, 1H), 5.67 (s, 1H), 4.50-4.42 (m, 1H), 1.67 (s, 3H), 1.04 (d, J=6.6 Hz, 3H), 1.03 (d, J=6.6 Hz, 3H). MS (ESI) 437 [M+H]+.

Provenance & Evidence