(2S)-Methyl 2-(7-(4-allylchroman-6-yl)-2-(2'-(allyloxy)-[1,1'-biphenyl]-3-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate → methyl (2S)-2-(4-methyl-21,29-dioxa-5,7,8-triazaheptacyclo[24.6.2.16,9.110,14.02,7.015,20.030,34]hexatriaconta-1(33),2,4,6(36),8,10,12,14(35),15,17,19,23,30(34),31-tetradecaen-3-yl)-2-[(2-methylpropan-2-yl)oxy]acetate

Participants

Reaction Conditions

Reaction Steps

A solution of (2S)-methyl 2-(7-(4-allylchroman-6-yl)-2-(2′-(allyloxy)-[1,1′-biphenyl]-3-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate (0.373 g, 0.567 mmol) in DCE (275 ml) was heated (70° C.) and then treated with Hoveyda-Grubbs cat.2nd gen. (0.025 g, 0.040 mmol). The reaction was stirred for 2.5 hrs, then additional catalyst (0.025 g, 0.040 mmol) was added, the temperature was raised (80° C.) and the reaction was stirred for 30 min. The reaction was cooled, concentrated, and the residue was purified by biotage (24 g SiO2, 0% (3 CV), 0-60% (15 CV), 60% (2 CV), EtOAc in hexanes) to afford the desired product (0.300 g, 0.476 mmol, 84% yield). LCMS (M+H)=630.5.

Provenance & Evidence