2-bromo-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde → 2-(5-(difluoromethoxy)-1-methyl-1H-indazol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde

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2-Bromo-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde (224 mg, 629 μmol) and 5-(difluoromethoxy)-1-methyl-3-(tributylstannyl)-1H-indazole (398 mg, 818 μmol.30) were dissolved in DMF (3 mL) under argon, tetrakis(triphenylphosphine)palladium (0) (36.3 mg, 31.4 μmol) and CuI (24.0 mg, 126 μmol, Eq: 0.20) were added and the mixture sonicated for 5 min with bubbling argon. The reaction mixture was stirred at 90° C. (oil bath temperature) for 2.5 h. The reaction mixture was concentrated under high vacuum and the residue was purified by chromatography (80 g column, 50 μm from Analogix, 0-50% EtOAc in hexanes over 30 min) to give 2-(5-(difluoromethoxy)-1-methyl-1H-indazol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde (217 mg, 458 μmol, 72.9%) as a light brown solid. MS (M+H)+=474; 1H NMR (CDCl3) δ: 10.51 (br. s., 1H), 9.29 (s, 1H), 8.61 (s, 1H), 8.30 (s, 1H), 7.38-7.52 (m, 1H), 7.27-7.36 (m, 1H), 6.69 (t, J=74.8 Hz, 1H), 5.76 (s, 2H), 4.20 (s, 3H), 3.56-3.70 (m, 2H), 0.91-1.02 (m, 2H), −0.08-0.06 (m, 9H).

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