Tetrahydrofuran → HCID 67325544, compound

Participants

Reaction Steps

Anhydrous dioxane was sparged with argon gas for 1 h before being used. Triisopropylsilanethiol (0.95 mL, 4.4 mmol) was dissolved into anhydrous 1,4-dioxane (3 mL) and to this 1.0 M lithium hexamethyldisilazide in THF (4.2 mL, 4.2 mmol) was added slowly. The reaction was stirred for 2.5 h. A portion of the lithium triisopropylsilanethiolate solution (2.64, 1.32 mmol) was added to a suspension of tert-butyl 7-iodo-1,3a,4,9b-tetrahydrochromeno[3,4-b]pyrrole-3(2H)-carboxylate P02 (480 mg, 1.2 mmol) and tetrakis(triphenylphosphine)palladium(0) (139 mg, 0.12 mmol) in 1,4-dioxane (2 mL) under argon. The reaction mixture was stirred at 60° C. for 16 h and the solvent was evaporated. The residue was triturated with anhydrous hexane, filtered through a plug of celite, and the filtrate concentrated to yield the crude product which was used in the next step without further purification. MS m/z 408 [M−tBu+H]+.

Provenance & Evidence