Triethylamine → Methyl (2S)-2-(tert-butoxy)-2-[4,23-dimethyl-11,22-dioxa-1,5,7,8-tetraazapentacyclo[21.2.2.16,9.02,7.013,18]octacosa-2,4,6(28),8,13(18),14,16,19-octaen-3-yl]acetate

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-methyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(((2-bromobenzyl)oxy)methyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate (0.025 g, 0.040 mmol) in acetonitrile (1 ml) in a pressure tube were added Et3N (0.055 ml, 0.397 mmol), triphenylphosphine (3.12 mg, 0.012 mmol) and tris(dibenzylideneacetone)dipalladium (0) (3.64 mg, 3.97 μmol). The tube was sealed and the mixture was stirred at 120° C. After 18 h, the dark mixture was cooled and concentrated. The brown residue was purified by flash chromatography (Biotage; 0%-60% EtOAc/hexane; 20 CV) to afford the title compound as mixture of cis- and trans-isomers (16.9 mg, 0.031 mmol, 78% yield) as a pale yellow oil. LCMS (M+H) calcd for C31H41N4O5: 549.30. found: 549.4.

Provenance & Evidence