2-Fluoro-4-iodoaniline → HCID 25070856, compound

Participants

Reaction Steps

LDA (2N solution in heptane/tetrahydrofuran/ethylbenzene, 6 mL, and 12 mmol) was added dropwise to a stirred solution of 2-fluoro-4-iodoaniline (2.085 g, 8.8 mmol) in THF (14 mL) at −78° C. After 10 minutes, a solution of example 6c (0.9 g, 3.57 mmol) in THF (30 mL) was then added at −78° C. The reaction mixture was allowed to warm to room temperature and stirred for 13 h. The solution was cooled to 0° C., quenched with 1N HCl (100 mL), extracted with EtOAc and dried (MgSO4). Purification by silica gel chromatography (10% MeOH/DCM) gave 340 mg (20%) of the title compound as light yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 12.72 (s, 1H), 8.41 (s, 1H), 7.73 (dd, 1H, J=10.4, 1.6 Hz), 7.55 (dd, 1H. J=8.4, 1.6 Hz), 7.49 (t, 1H, J=8.4 Hz), 7.03 (dd, 1H, J=10.4, 1.6 Hz), 6.62 (dd, 1H, J=10.4, 1.6 Hz), 3.32-3.42 (m, 1H), 2.54-2.53 (m, 3H), 1.35-1.42 (m, 2H), 0.84-0.89 (m, 2H). MS (ES) [m+H] calc'd for C19H15F2IN2O2, 469; found 469.

Provenance & Evidence