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N-[5-[4-Amino-1-(phenylsulfonyl)-1H-indazol-6-yl]-2-(methyloxy)-3-pyridinyl]methanesulfonamide (750 mg, 1.584 mmol) was dissolved in DCM (20 ml), cooled to 0° C. before pyridine (0.192 mL, 2.376 mmol) was added. 6-(chloromethyl)-2-pyridinecarbonyl chloride (354 mg, 1.584 mmol) in DCM (10 ml) was then added dropwise over 15 mins and the reaction was stirred at 0° C. for 2 hr; ice was allowed to melt over this time. Saturated aqueous sodium bicarbonate solution (20 ml) was added to the mixture and it was stirred vigourously for 10 mins. The organic layer was separated using a hydrophobic frit, washed with water (20 ml) and concentrated in vacuo to give an orange oil. The oil was triturated with ether and the resulting solid was filtered off then pre-adsorbed onto silica. The silica was added to the top of a 50 g silica SPE cartridge that was subsequently eluted with 0-100% EtOAc/cyclohexane over 60 mins to afford the title compound as a pale yellow solid (253 mg).

1. additionwas added
2. stirringwas stirred vigourously for 10 mins
3. customThe organic layer was separated
4. washwashed with water (20 ml)
5. concentrationconcentrated in vacuo
6. customto give an orange oil
7. customThe oil was triturated with ether
8. filtrationthe resulting solid was filtered off
9. additionThe silica was added to the top of a 50 g silica SPE cartridge that
10. washwas subsequently eluted with 0-100% EtOAc/cyclohexane over 60 mins