4-Fluoroaniline → HCID 90409046, compound

Participants

Reaction Conditions

Reaction Steps

7,8-Dihydro-2-(4-acetylbenzyl)-3-chloro-5,7,7-trimethyl-[2H]-imidazo-[1,2-a]pyrazolo[4,3-e]pyrimidin-4(5H)-one (150 mg, 0.389 mmol), 4-fluorobenzenamine (41 μL, 0.428 mmol) and potassium carbonate (107 mg, 0.775 mmol) in tert-amyl alcohol (1.3 mL) are degassed with argon and then Xantphos (9.0 mg, 0.016 mmol) and Pd2(dba)3 (7.13 mg, 0.0078 mmol) are added. The suspension is degassed again, and then heated to 110° C. The reaction mixture is stirred at 110° C. under argon for 24 h. After routine workup, the crude mixture is purified with a semi-preparative HPLC to give 107 mg of the final product as a formate salt (HPLC purity: 96%; yield: 54%). 1H NMR (500 MHz, Chloroform-d) δ 8.20 (s, 1H), 7.84 (d, J=8.3 Hz, 2H), 7.06-7.00 (m, 3H), 6.99-6.92 (m, 2H), 6.92-6.86 (m, 2H), 4.91 (s, 2H), 3.77 (s, 2H), 3.37 (s, 3H), 2.57 (s, 3H), 1.48 (s, 6H). MS (ESI) m/z 461.2 [M+H]+.

Provenance & Evidence