Sodium Cyanide → 5,7-Dimethyl-1H-indazole-3-carbonitrile

Participants

Reaction Conditions

Reaction Steps

Iodide 3 (20 g, 74.0 mmol) was dissolved in anhydrous NMP (300 mL). To this solution were added CuCN (19.9 g, 222 mmol, 3 eq) and NaCN (7.25 g, 148 mmol, 2 eq) and the mixture was heated at 130 ° C. for 18 h under an inert atmosphere. This solution was then poured into 0.25 M KH2PO4 (1.5 L) and Et2O (750 mL) and Celite (˜100g) were added. The suspension was stirred vigorously for 0.5 h then filtered through a sintered glass funnel. The phases were separated and the aqueous layer extracted with Et2O (3×200 mL). The combined organic extracts were washed with H2O (2×200 mL), brine (1×200 mL), dried (MgSO4), filtered and concentrated provide 8.3g (65% yield) of 5,7-dimethyl-1H-indazole-3-carbonitrile 4. The nitrile was used as is for the next reaction. RP-HPLC Method: 2-100% B in 2 minutes.

Provenance & Evidence