Sodium Iodide → HCID 71280330, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2-bromo-N-tert-butyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (150 mg, 351 μmol) in toluene (1 mL) was added copper(I) iodide (3.52 mg, 39.3 μmol), sodium iodide (105 mg, 702 μmol) and trans-N,N′-dimethylcyclohexane-1,2-diamine (12.7 mg, 89.5 μmol). The reaction mixture was sealed under nitrogen and the mixture heated at 110° C. for 15 h. 5-(Difluoromethoxy)-1H-indazole (64.6 mg, 351 μmol) and potassium phosphate tribasic (156 mg, 737 μmol) were added then the mixture was degassed 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 N-tert-butyl-2-(5-(difluoromethoxy)-1H-indazol-1-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (130 mg, 70%). 1H NMR (CDCl3) δ: 9.18 (s, 1H), 8.61 (d, J=9.0 Hz, 1H), 8.36 (s, 1H), 8.27 (s, 1H), 7.69 (s, 1H), 7.59 (s, 1H), 7.32 (dd, J=9.0, 2.1 Hz, 1H), 6.27-6.89 (m, 1H), 5.72 (s, 2H), 3.53-3.66 (m, 2H), 1.61 (s, 9H), 0.87-1.07 (m, 2H), −0.03 (s, 9H).

Provenance & Evidence