Hydrochloric Acid → HCID 58337495, compound

Participants

Reaction Conditions

Reaction Steps

CuCl2 (47.5 mg, 0.353 mmol, 1.20 eq) was dissolved in acetonitrile (2 mL) in a flame-dried 3-neck flask flushed with argon and equipped with a condenser. t-Butyl nitrite (45.5 mg, 0.441 mmol, 1.50 eq) was added and the reaction heated at 55° C. Compound 2 (100 mg, 0.294 mmol, 1.00 eq) was dissolved in acetonitrile (0.1 mL) and added dropwise to the reaction. After 10 minutes the reaction was cooled to rt, poured into 20% HCl and extracted with CH2Cl2 (3×). The combined organics were dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography on silica gel afforded 67 mg (63%) of the title compound as a pale yellow solid: 1H NMR (400 MHz, DMSO-d6) 10.50 (s, 1H), 8.47 (d, J=2.8 Hz, 1H), 8.45 (dd, J=4.6, 1.3 Hz, 1H), 7.96 (t, J=1.8 Hz, 1H), 7.86 (dt, J=7.9, 1.2 Hz, 1H), 7.77 (t, J=1.8 Hz, 1H), 7.68-7.66 (m, 1H), 7.58 (ddd, J=8.4, 3.0, 1.5 Hz, 1H), 7.56 (t, J=7.9 Hz, 1H), 7.48 (dd, J=8.4, 4.6 Hz, 1H), 7.40 (t, J=2.0 Hz, 1H), 6.94 (t, J=2.0 Hz, 1H); ES-MS [M+1]+: 359.0.

Provenance & Evidence