Dimethylformamide → HCID 86761703, compound

Participants

Reaction Conditions

Reaction Steps

A DMF solution (4 mL) containing the intermediate from Step B (453 mg, 1.47 mmol), INTERMEDIATE 1 (607 mg, 1.62 mmol), Bu4NCl (817 mg, 2.94 mmol), LiOAc (242 mg, 3.67 mmol), LiCl (62 mg, 1.47 mmol) and Pd(OAc)2 (17 mg, 0.076 mmol) was stirred overnight at 90° C. under an argon atmosphere. The solution was partitioned between water and ethyl acetate. The organic phase was washed with water (3×), brine and dried over MgSO4. The solution was filtered, concentrated and the residue purified by silica gel chromatography using a hexanes/ethyl acetate gradient to give the title compound. 1H NMR (400 MHz, CDCl3): δ 9.67 (s, 1H); 7.63 (d, J=8.2 Hz, 2H); 7.50 (d, J=8.6 Hz, 2H); 7.39-7.33 (m, 2H); 7.29-7.24 (m, 3H); 7.15-7.08 (m, 3H); 6.79 (broad s, 1H); 3.66 (q, J=5.9 Hz, 2H); 3.61-3.55 (m, 1H); 3.03-2.97 (m, 2H); 2.85-2.81 (m, 2H); 2.53 (t, J=5.9 Hz, 2H); 1.42 (s, 9H). LCMS1 4.00 min. (M+H)=500.

Provenance & Evidence