Cesium carbonate → HCID 131736367, compound

Participants

Reaction Conditions

Reaction Steps

Cs2CO3 (9.58 g, 29.4 mmol, Eq: 1.5) was added to a mixture of 3-(bromomethyl)-1-(2-cyanophenyl)-1H-indole-2-carbonitrile (9.89 g, 29.4 mmol, Eq: 1.5) and tert-butyl methyl((S)-1-oxo-1-((S)-4-oxo-2′,3′,4,5,5′,6′-hexahydro-3H-spiro[benzo[b][1,4]oxazepine-2,4′-pyran]-3-ylamino)propan-2-yl)carbamate (8.5 g, 19.6 mmol, Eq: 1.00) in DMF (20 mL) and the mixture heated to 70° C. for 1 h. The mixture was cooled, diluted with sat. NH4Cl and extracted with EtOAc. The combined extracts were washed with H2O, dried over Na2SO4 and concentrated to give a material that was purified by silica gel chromatography to afford tert-butyl (S)-1-((S)-5-((2-cyano-1-(2-cyanophenyl)-1H-indol-3-yl)methyl)-4-oxo-2′,3′,4,5,5′,6′-hexahydro-3H-spiro[benzo[b][1,4]oxazepine-2,4′-pyran]-3-ylamino)-1-oxopropan-2-yl(methyl)carbamate (13 g, 96.3%) as a light yellow solid.

Provenance & Evidence