Aniline → HCID 86650288, compound

Participants

Reaction Steps

A suspension of tert-butyl (8R)-9-allyl-8-(3,5-difluorophenyl)-8-methyl-10-oxo-6,9-diazaspiro[4.5]decane-6-carboxylate described in Intermediate 3 (0.292 g, 0.694 mmol) and 5-bromo-1′-{[2-(trimethylsilyl)ethoxy]methyl}-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one described in Intermediate 13 (309 mg, 0.694 mmol Palladium(II) acetate (46.8 mg, 0.208 mmol), sodium acetate (0.57 mg, 0.694 mmol), and tris-2 methoxy phenyl phosphine (122 mg, 0.347 mmol), in DMF (3 ml) was microwaved at 130° C. for 1 hour. The mixture was filtered through a plug of celite, washing with water and ethyl acetate. The layers were separated, then the aqueous layer was washed with 3×30 mL EtOAc. The combine organic layers were washed with brine, then dried over sodium sulfate, filtered and concentrated in vacuo. The oily residue was purified on a 40 g redisep column, eluting with ethyl acetate:hexanes, 0:100 to 50:50. The desired fractions were concentrated in vacuo to yield the title compound. MS: m/z=785 (M+1).

Provenance & Evidence