Sodium Iodide → HCID 71280168, compound

Participants

Reaction Conditions

Reaction Steps

2-Bromo-N-(1-hydroxy-2-methylpropan-2-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (110 mg, 248 μmol) was dissolved in toluene (1.4 mL) and copper (I) iodide (2.49 mg, 27.8 μmol), sodium iodide (74.4 mg, 496 μmol) and trans-N,N′-dimethylcyclohexane-1,2-diamine (9.00 mg, 63.3 μmol) added. The mixture was sealed under nitrogen and the mixture heated at 110° C. for 15 h. 5-fluoro-1H-indazole (33.8 mg, 248 μmol) and potassium phosphate tribasic (111 mg 521 μmol) were added, the mixture degassed with nitrogen, and the mixture heated at in sealed tube at 110° C. for 15 h. The mixture was filtered, the cake washed with ethyl acetate, and the filtrate concentrated in vacuo. Purification by chromatography (silica, 24 g Analogix column, 0-40% ethyl acetate in hexanes) gave 2-(5-Fluoro-1H-indazol-1-yl)-N-(1-hydroxy-2-methylpropan-2-yl)-5((2(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (111 mg, 90%). 1H NMR (CDCl3) δ: 9.19 (s, 1H), 8.55 (dd, J=9.1, 4.2 Hz, 1H), 8.37 (s, 1H), 8.26 (s, 1H), 7.92 (s, 1H), 7.49 (dd, J=8.1, 2.3 Hz, 1H), 7.28-7.33 (m, 1H), 5.73 (s, 2H), 3.81 (s, 2H), 3.53-3.66 (m, 2H), 1.54 (s, 6H), 0.91-1.01 (m, 2H), −0.02 (s, 9H).

Provenance & Evidence