Acryloyl chloride → HCID 86651985, compound

Participants

Reaction Steps

A dry round-bottom flask was charged with N1,N1,N2-trimethylethane-1,2-diamine (0.32 mL, 2.50 mmol), diisopropylethylamine (0.87 mL, 5.00 mmol) and CH2Cl2 (12 mL) and the solution cooled with an ice-water bath. Acryloyl chloride (0.20 mL, 2.50 mmol) was added dropwise and the reaction allowed to warm to room temperature. After 3 hours the solvent was removed and the residue purified by column chromatography (silica gel, 88:10:2, CH2Cl2/MeOH/7M NH3 in MeOH) to give 50 mg of a crude oil to which was added 3-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole-6-carbaldehyde (105 mg, 0.262 mmol), DMF (5 mL) and diisopropylethylamine (0.091 mL, 0.524 mmol). The mixture was degassed by bubbling Argon through the solution for 15 min. Pd(OAc)2 (3.0 mg, 0.013 mmol) and P(o-tolyl)3 (12 mg, 0.039 mmol) were then added and the reaction heated to 110° C. for 18 hours. The mixture was cooled to room temperature, NaHCO3(sat.) (5 mL) was added, and the product extracted (3×) with EtOAc. The organic layer was washed with water (2×) and brine (2×), and then dried over MgSO4. After removal of solvent the residue was purified by column chromatography (silica gel, 93:6:1, CH2Cl2/MeOH/7M NH3 in MeOH) to give 41 mg, 41% of a red-orange oil. MS ESI 431.2 [M+H]+, calcd for [C22H34N4O3Si+H]+ 431.25.

Provenance & Evidence