Diisopropylamine → HCID 58382050, compound

Participants

Reaction Conditions

Reaction Steps

1-Methyl-4-iodo-pyrazole (18) (5.0 g 24.04 mmole) was dissolved in DMF (32 mL) and ethynyltrimethylsilane (4.76 mL, 3.31 g, 33.7 mmole) was added followed by diisopropylamine (4.46 mL, 3.21 g 31.78 mmole), copper(I) iodide (304 mg 1.59 mmole) and triphenylphosphine (1.26 g 4.81 mmole). The reaction was flushed with argon. Palladium acetate (351 mg 1.56 mmole) was added and the reaction was again flushed with argon. It was heated at 60° C. for 60 mins. The reaction was cooled, added to water (350 ml) and extracted with ether (3×100 mL). The organic solution was filtered from a brown solid which was washed with a little more ether. The organic solution was washed with water (3×80 mL), brine, dried and evaporated. The crude product was flash chromatographed (silica) using 1:4 ethyl acetate:cyclohexane and then 1:3 ethyl acetate:cyclohexane to give the title compound as a solid (2.85 g 67%). 1H-NMR (CDCl3, 500 MHz): δ 0.24 (s, 9H), 3.87 (s, 3H), 7.50 (s, 1H), 7.58 (s, 1H).

Provenance & Evidence