HCID 53307538, compound → HCID 53307539, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of Example 1 (94 mg, 0.237 mmol) and PdCl2(dppf) (18 mg, 0.047 mmol) in THF (1 ml) at room temperature was added ZnMe2 in toluene (1.2 M, 0.4 mL). The reaction mixture was stirred at 50° C. for 2 h. A second portion of ZnMe2 (0.6 mL) and PdCl2(dppf) (18 mg) was added. The reaction was heated at 50° C. for 3 h, cooled and quenched by sat. aqueous NaHCO3. The mixture was extracted with EtOAc, dried over Na2SO4, filtered and concentrated. Purification by reverse-phase HPLC (C-18 column, 5-90% MeCN in H2O with both containing 0.05% TFA) provided the title compound. 1H NMR (400 MHz, CDCl3) δ 8.46 (d, J=2.0 Hz, 1H), 8.27 (d, J=7.6 Hz, 1H), 8.13 (s, 1H), 8.13 (d, J=8.0 Hz, 1H), 8.02 (d, J=7.6 Hz, 1H), 7.75 (t, J=8.0 Hz, 1H), 7.60 (d, J=7.6, 1H), 7.30 (dd, J=2.4, 8.0 Hz, 1H), 7.04 (d, J=8.0 Hz, 2H), 4.45 (s, 2H), 3.92-3.84 (m, 1H), 3.61-3.57 (m, 1H), 2.51 (s, 3H), 2.17-2.12 (m, 2H), 1.82-1.79 (m, 2H), 1.54-1.23 (m, 4H). HRMS (ES) [M+1]+ calcd for C23H25N3O2: 376.2020, Found: 376.2010.

Provenance & Evidence