1,1,1-trifluoro-2-phenylbut-3-yn-2-ol

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

Procedure: (2S)-2-tert-butoxy-2-(1-(4-chlorophenyl)-3-methyl-7-(4,4,4-trifluoro-3-hydroxy-3-phenylbut-1-ynyl)naphthalen-2-yl)acetic acid was prepared by the method in Example 8 from ethyl 2-(7-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-tert-butoxyacetate and 1,1,1-trifluoro-2-phenylbut-3-yn-2-ol. 1H-NMR: 400 MHz, (CD3OD) δ: 7.74 (m, 3H), 7.67 (s, 1H), 7.55 (m, 4H), 7.46 (m, 2H), 7.39 (m, 2H), 7.33 (m, 1H), 5.07 (s, 1H), 2.66 (s, 3H), 0.94 (s, 9H). LCMS-ESI+ (m/z): [M-OH]+ calcd for C31H32ClF3O3: 563.2. found: 563.1.

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

Procedure: (2S)-2-tert-butoxy-2-(1-(4-chlorophenyl)-3-methyl-7-(4,4,4-trifluoro-3-hydroxy-3-phenylbut-1-ynyl)naphthalen-2-yl)acetic acid was prepared by the method in Example 8 from ethyl 2-(7-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-tert-butoxyacetate and 1,1,1-trifluoro-2-phenylbut-3-yn-2-ol. 1H-NMR: 400 MHz, (CD3OD) δ: 7.74 (m, 3H), 7.67 (s, 1H), 7.55 (m, 4H), 7.46 (m, 2H), 7.39 (m, 2H), 7.33 (m, 1H), 5.07 (s, 1H), 2.66 (s, 3H), 0.94 (s, 9H). LCMS-ESI+ (m/z): [M-OH]+ calcd for C31H32ClF3O3: 563.2. found: 563.1.

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

Procedure: Same procedure as that described in example 5, stage 5.4, starting from 0.4 g (0.95 mmol) of 2-amino-7-chloro-1-ethyl-3-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-1H-[1,8]naphthyridin-4-one, 0.4 g (1.9 mmol) 1,1,1-trifluoro-2-phenyl-but-3-yn-2-ol, 33 mg (0.05 mmol), bis(triphenylphosphine)palladium(II) dichloride, 18 mg (0.1 mmol) copper (I) iodide, 3 ml DMF (degassed), 3 ml triethylamine (degassed). 0.15 g of the title compound is obtained.

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

Procedure: Same procedure as that described in example 5, stage 5.4, starting from 0.4 g (0.95 mmol) of 2-amino-7-chloro-1-ethyl-3-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-1H-[1,8]naphthyridin-4-one, 0.4 g (1.9 mmol) 1,1,1-trifluoro-2-phenyl-but-3-yn-2-ol, 33 mg (0.05 mmol), bis(triphenylphosphine)palladium(II) dichloride, 18 mg (0.1 mmol) copper (I) iodide, 3 ml DMF (degassed), 3 ml triethylamine (degassed). 0.15 g of the title compound is obtained.

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

Procedure: (2S)-2-tert-butoxy-2-(1-(4-chlorophenyl)-3-methyl-7-(4,4,4-trifluoro-3-hydroxy-3-phenylbut-1-ynyl)naphthalen-2-yl)acetic acid was prepared by the method in Example 8 from ethyl 2-(7-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-tert-butoxyacetate and 1,1,1-trifluoro-2-phenylbut-3-yn-2-ol. 1H-NMR: 400 MHz, (CD3OD) δ: 7.74 (m, 3H), 7.67 (s, 1H), 7.55 (m, 4H), 7.46 (m, 2H), 7.39 (m, 2H), 7.33 (m, 1H), 5.07 (s, 1H), 2.66 (s, 3H), 0.94 (s, 9H). LCMS-ESI+ (m/z): [M-OH]+ calcd for C31H32ClF3O3: 563.2. found: 563.1.