Hydrochloric Acid → HCID 58789348, compound

Participants

Reaction Conditions

Reaction Steps

N-isobutyl-2-(3-methoxy-4-(4-methylthiophen-3-yl)phenyl)-2-methylpropanamide (example 35a) (103 mg, 0.3 mmol) was dissolved in dry DCM (5 mL), the mixture was under argon cooled to −78° C. and BBr3 (1.69 mL of 1M solution in DCM) was added drop-wise and the mixture was stirred at room temperature for 72 hrs. The solution was diluted with DCM and treated with 1M aq. HCl. The organic phase was washed with water and brine, dried over MgSO4 filtered and evaporated. The residue was purified on preparative RP HPLC (acetonitrile/water) and on silica gel (EtOAc/hexanes) and the product was co-evaporated with ethanol to give 2-(3-hydroxy-4-(4-methylthiophen-3-yl)phenyl)-N-isobutyl-2-methylpropanamide (69 mg, 70%). 1H NMR (400 MHz, dMSO): δ 0.74-0.76 (d, 6H), 1.42 (s, 6H), 1.67-1.74 (m, 1H), 2.09 (s, 3H), 2.83-2.86 (t, 2H), 6.76-6.78 (dd, 1H), 6.87-6.88 (d, 1H), 7.01-7.03 (d, 1H), 7.13-7.14 (m, 1H), 7.21-7.22 (d, 1H), 7.27-7.29 (t, 1H), 9.38-9.39 (b, 1H); MS (332).

Provenance & Evidence