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2-(6-Chloro-1H-indazol-3-yl)-N-isopropyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (120 mg, 247 μmol) was dissolved in DMF (1 mL) and cooled to 0° C. Sodium hydride (12.9 mg, 322 μmol) was added and the mixture was stirred for 30 min. Benzyl bromide (63.5 mg, 44.1 μL, 371 μmol) was added and the mixture was warmed to 20° C. After 15 h the mixture was diluted with water and extracted with ethyl acetate. The organic extracts were washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by chromatography (silica, 40 g Analogix column, 20-50% ethyl acetate in hexanes, 15 min gradient) to give 2-(1-benzyl-6-chloro-1H-indazol-3-yl)-N-isopropyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (87 mg, 151 μmol, 61.1%) as a pale yellow powder. 1H NMR (CDCl3) δ: 9.29 (s, 1H), 8.48 (d, J=8.7 Hz, 1H), 8.38 (s, 1H), 8.20 (d, J=7.9 Hz, 1H), 7.43 (d, J=1.5 Hz, 1H), 7.20-7.39 (m, 6H), 5.73 (s, 2H), 5.68 (s, 2H), 4.38-4.55 (m, 1H), 3.52-3.64 (m, 2H), 1.42 (d, J=6.4 Hz, 6H), 0.86-1.00 (m, 2H), −0.03 (s, 9H).

1. temperaturethe mixture was warmed to 20° C
2. extractionextracted with ethyl acetate
3. washThe organic extracts were washed with brine
4. dry with materialdried over anhydrous sodium sulfate
5. concentrationconcentrated in vacuo
6. customThe residue was purified by chromatography (silica, 40 g Analogix column, 20-50% ethyl acetate in hexanes, 15 min gradient)