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In a 10 mL pear-shaped flask, 2-(6-chloro-1H-indazol-3-yl)-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-2-(3-cyano-azetidin-1-yl)-1-methyl-2-oxo-ethyl]-amide (280 mg, 0.48 mmol) was combined with DMF (8 ml) at 0° C. to give a yellow solution. Sodium hydride (60% in mineral oil, 70 mg, 1.74 mmol) was added and the reaction was stirred at 0° C. for 10 min. Dimethylaminoethyl bromide hydrobromide (169 mg, 0.73 mmol) was added and the reaction was stirred at 0° C. for 30 min then allowed to warm up to room temperature and stirred for 2 h. The reaction was quenched with 5 ml of brine and 10 ml of water then extracted with EtOAc (2×). The combined organics were washed with water and brine then dried and purified by SiO2 chromatography (0% to 10% MeOH/CH2Cl2 to isolate 135 mg (43%) of 2-[6-chloro-1-(2-dimethylamino-ethyl)-1H-indazol-3-yl]-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-2-(3-cyano-azetidin-1-yl)-1-methyl-2-oxo-ethyl]-amide as a foaming solid. MS: (M+H)+=651.

1. customto give a yellow solution
2. stirringthe reaction was stirred at 0° C. for 30 min
3. temperatureto warm up to room temperature
4. stirringstirred for 2 h
5. customThe reaction was quenched with 5 ml of brine and 10 ml of water
6. extractionthen extracted with EtOAc (2×)
7. washThe combined organics were washed with water and brine
8. customthen dried
9. custompurified by SiO2 chromatography (0% to 10% MeOH/CH2Cl2