Sodium bis(trimethylsilyl)amide → HCID 118415188, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 6-chloro-3,3-dimethyl-1H-pyrrolo[2,3-b]pyridin-2(3H)-one (150 mg, 763 mol), cyclopropylboronic acid (131 mg, 1.53 mmol), copper (II) acetate (145 mg, 801 μmol) and DMAP (280 mg, 2.29 mmol) in toluene (15 ml) was added sodium bis(trimethylsilyl)amide (2 M in THF, 400 μl, 801 μmol). While bubbling dry air through the reaction mixture, it was heated to 95° C. and stirred for 16 hours. The reaction mixture was poured into 1 M aqueous HCl solution (20 ml) and extracted with tBuOMe. The organic layers were washed with 1 M aqueous HCl solution and brine, dried over Na2SO4 and concentrated in vacuo. The crude material was purified by silica gel chromatography using heptane/ethyl acetate as eluent. The title compound was obtained as yellow viscous oil (178 mg).

Provenance & Evidence