Dimethylacetamide → HCID 10105314, compound

Participants

Reaction Steps

A solution of 6-iodo-1-isopropyl-1H-indazole (49.6 mg, 0.17 mmol), tris-(dibenzylidenacetone)dipalladium(0) (8 mg, 8.7 μmol), S-BINAP (9 mg, 15 μmol), potassium bis(trimethylsilyl)amide (75 mg, 0.37 mmol) and N,N-dimethyl-acetamide (45 μL, 0.48 mmol) in 1,4-dioxane (2.5 mL) was heated at 100° C. for 2 h. After cooling to room temperature, the reaction mixture was diluted with water (1 mL) and passed through an EXTUBE using dichloromethane to elute (10 mL). LiAlH4 (0.4 mL, 1M, 0.4 mmol) was added to a solution of the crude product in THF (2.5 mL) and the reaction mixture heated at reflux for 2 h. After cooling to room temperature, the mixture was quenched with Rochelle's salt (1 M, 1 mL) and silica gel (to absorb water) and passed through a frit using methanolic ammonia in dichloromethane (0-10%). The 5% fraction was further purified by flash chromatography (silica gel, 2-8% methanolic ammonia in dichloromethane) to give the product (5.9 mg).

Provenance & Evidence