2-tert-Butyl-1,1,3,3-tetramethylguanidine → 3-iodo-4-nitro-1-(pyridin-3-ylmethyl)-1H-indazole

Participants

Reaction Steps

To a flask was added 3-iodo-4-nitro-1H-indazole (0.300 g, 1.04 mmol) and 4-(bromomethyl)pyridine hydrobromide (0.315 g, 1.25 mmol) which were slurried in CH3CN (5.0 mL). 2-tert-Butyl-1,1,3,3-tetramethylguanidine (0.460 mL, 2.28 mmol) was added and the mixture was stirred overnight. The mixture was diluted with water (20 mL) and stirred for 15 minutes and filtered. The collected solids were washed with water followed by Et2O and hexanes, and dried under vacuum to provide the title compound as a brown powder (0.304 g, 71%), which was used directly in the subsequent step.

Provenance & Evidence