7-fluoro-2,3-dihydroinden-1-one

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a room temperature solution of aluminum chloride (11.77 g, 88 mmol) in dichloroethane (100 mL) was added 7-fluoro-2,3-dihydro-1H-inden-1-one (5.3 g, 35.3 mmol) followed with bromine (1.91 mL, 37.1 mmol). The mixture was heated at 65° C. for 16 hours, then cooled to ambient temperature and poured into a mixture of ice and HCl (1N aqueous). The mixture was extracted twice with ether (200 mL). The combined organic extracts were dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was purified by chromatography (silica gel column eluting with 0-10% EtOAc/hexanes) to provide the title compound (5.2 g, 64%). MS (DCI/NH3) m/z 246 (M+NH4)+. cooled to ambient temperature The mixture was extracted twice with ether (200 mL) The combined organic extracts were dried (MgSO4) filtered concentrated under reduced pressure The residue was purified by chromatography (silica gel column eluting with 0-10% EtOAc/hexanes)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The reductive amination of (S)-2-amino-6-(5-amino-2-fluoro-phenyl)-3,5,5,6-tetramethyl-5,6-dihydro-3H-pyrimidin-4-one (intermediate J) and 7-fluoro-indan-1-one using decaborane yielded a mixture of epimers of the title compound as a white foam. MS (ESI): m/z=430.3 [M+H]+. yielded

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The reductive amination of (S)-2-amino-6-(5-amino-2-fluoro-phenyl)-3,5,5,6-tetramethyl-5,6-dihydro-3H-pyrimidin-4-one (intermediate J) and 7-fluoro-indan-1-one using decaborane yielded a mixture of epimers of the title compound as a white foam. MS (ESI): m/z=430.3 [M+H]+. yielded

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The reductive amination of (S)-2-amino-6-(5-amino-2-fluoro-phenyl)-3,5,5,6-tetramethyl-5,6-dihydro-3H-pyrimidin-4-one (intermediate J) and 7-fluoro-indan-1-one using decaborane yielded a mixture of epimers of the title compound as a white foam. MS (ESI): m/z=430.3 [M+H]+. yielded

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a room temperature solution of aluminum chloride (11.77 g, 88 mmol) in dichloroethane (100 mL) was added 7-fluoro-2,3-dihydro-1H-inden-1-one (5.3 g, 35.3 mmol) followed with bromine (1.91 mL, 37.1 mmol). The mixture was heated at 65° C. for 16 hours, then cooled to ambient temperature and poured into a mixture of ice and HCl (1N aqueous). The mixture was extracted twice with ether (200 mL). The combined organic extracts were dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was purified by chromatography (silica gel column eluting with 0-10% EtOAc/hexanes) to provide the title compound (5.2 g, 64%). MS (DCI/NH3) m/z 246 (M+NH4)+. cooled to ambient temperature The mixture was extracted twice with ether (200 mL) The combined organic extracts were dried (MgSO4) filtered concentrated under reduced pressure The residue was purified by chromatography (silica gel column eluting with 0-10% EtOAc/hexanes)