2-Fluoro-4-iodoaniline → HCID 25070529, compound

Participants

Reaction Steps

LDA (2N solution in heptane/tetrahydrofuran/ethylbenzene, 0.39 mL, 0.77 mmol) was added dropwise to a stirred solution of 2-fluoro-4-iodoaniline (165 mg, 0.70 mmol) in THF (1.2 mL) at −78° C. After 15 minutes, a solution of example 1d (100 mg, 0.35 mmol) in NMP (1.8 mL) was then added at −78° C. The reaction mixture was allowed to warm to room temperature and stirred for 25 h. Purification by preparative HPLC mass triggered gave 7.6 mg (5%) of the title compound as yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 13.92 (s, 1H), 10.39 (s, 1H), 8.71 (s, 1H), 8.11 (t, 1H, J=11.2 Hz), 7.65 (d, 1H, J=10.4 Hz), 7.44 (d, 1H, J=8.4 Hz), 6.74-6.79 (m, 1H), 4.12-4.19 (m, 1H), 1.15-1.22 (m, 4H). MS (ES) [m+H] calc'd for C19H12F3IN2O3, 501; found 501.

Provenance & Evidence