Stannous Chloride → HCID 178448264, compound

Participants

Reaction Conditions

Reaction Steps

The product from Step A (74 mg, 0.14 mmol) was suspended in concentrated HCl (1 mL) then cooled to 0° C. To the stirred suspension was added a solution of NaNO2 (7.5 mg, 0.11 mmol) in water, then the mixture was stirred for 30 minutes. Solid SnCl2 (47 mg, 0.25 mmol) was added, then the mixture was stirred for another 30 minutes. Ice was added, then the mixture was extracted with EtOAc. The organic phase was washed with water then saturated NaCl(aq), dried over Na2SO4, filtered, then concentrated. The residue was purified by reverse phase HPLC eluting with 10-70% acetonitrile/water+0.1% TFA. Following lyophilization, this afforded the title compound as a white solid. 1H NMR (500 MHz, CDCl3): δ 7.51 (d, J=7.9 Hz, 2H); 7.43 (d, J=8.1 Hz, 2H); 7.31 (d, J=8.2 Hz, 2H); 7.26 obs, 2H); 7.17 (s, 1H); 6.85-6.78 (m, 2H); 4.60 (d, J=11.6 Hz, 1H); 3.76-3.62 (m, 3H); 2.70 (t, J=5.6 Hz, 2H); 2.41 (s, 3H); 1.59-1.43 (m, 2H); 1.07-0.96 (m, 2H); 0.73 (t, J=7.3 Hz, 3H). LC1 2.36 min. (M+H)+ 522.

Provenance & Evidence