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0 °C

6-Chloro-3-iodo-1-trityl-1H-pyrazolo[4,3-c]pyridine-4-carbaldehyde (10.26 g, 18.66 mmol) was dissolved in DCM (250 mL) and methanol (125 mL). The reaction mixture was then cooled to 0° C. and sodium borohydride (0.706 g, 18.66 mmol) was added. The reaction mixture was stirred at room temperature for 15 min. The reaction was quenched with water and extracted with DCM. The combined organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo while loading on silica gel. Purification by flash chromatography (2-10% DCM/EtOAc) gave (6-chloro-3-iodo-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)methanol (7.09 g, 12.85 mmol, 69%). MS ESI calc'd. for C26H19ClN3O [M+H]+ 552. found 552.

1. customThe reaction was quenched with water
2. extractionextracted with DCM
3. washThe combined organic layer was washed with brine
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customPurification by flash chromatography (2-10% DCM/EtOAc)