Dimethylacetamide → HCID 10105314, compound

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).

1. washto elute (10 mL)
2. temperaturethe reaction mixture heated
3. temperatureat reflux for 2 h
4. temperatureAfter cooling to room temperature
5. customthe mixture was quenched with Rochelle's salt (1 M, 1 mL) and silica gel (to absorb water)
6. customThe 5% fraction was further purified by flash chromatography (silica gel, 2-8% methanolic ammonia in dichloromethane)

ORD record

ord-31155bd56edc408f8f83e6496ac5948f

Source dataset

uspto-grants-2004_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06716837B1