N-cyclopropyl-3-iodobenzamide

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 6-bromo-1-morpholinophthalazine (95 mg, 323 μmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium dichloride (24 mg, 32 μmol), potassium acetate (95 mg, 969 μmol), and 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (90 mg, 355 μmol) was added 1,4-dioxane (3.23 mL) before it was heated to 80° C. for 2.5 h. This reaction mixture was added to a mixture of N-cyclopropyl-3-iodobenzamide (111 mg, 388 μmol) and tetrakis(triphenylphosphine) palladium (37 mg, 32 μmol) in ethanol (3.23 mL) and potassium carbonate −1.5 M in water (861 μl, 1292 μmol) and stirred for 2 h at 80° C. The mixture was diluted with 75 mL of ethyl acetate, added to a separation funnel, partitioned with sodium bicarbonate (saturated, aqueous), washed 2× with 50 mL of sodium bicarbonate (saturated, aqueous), separated, dried over sodium sulfate, concentrated in vacuo, and purified by HPLC to give the title compound. MS (ES+): 375 (M+H)+. added to a separation funnel partitioned with sodium bicarbonate (saturated, aqueous) washed 2× with 50 mL of sodium bicarbonate (saturated, aqueous) separated dried over sodium sulfate concentrated in vacuo purified by HPLC

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 6-bromo-1-morpholinophthalazine (95 mg, 323 μmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium dichloride (24 mg, 32 μmol), potassium acetate (95 mg, 969 μmol), and 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (90 mg, 355 μmol) was added 1,4-dioxane (3.23 mL) before it was heated to 80° C. for 2.5 h. This reaction mixture was added to a mixture of N-cyclopropyl-3-iodobenzamide (111 mg, 388 μmol) and tetrakis(triphenylphosphine) palladium (37 mg, 32 μmol) in ethanol (3.23 mL) and potassium carbonate −1.5 M in water (861 μl, 1292 μmol) and stirred for 2 h at 80° C. The mixture was diluted with 75 mL of ethyl acetate, added to a separation funnel, partitioned with sodium bicarbonate (saturated, aqueous), washed 2× with 50 mL of sodium bicarbonate (saturated, aqueous), separated, dried over sodium sulfate, concentrated in vacuo, and purified by HPLC to give the title compound. MS (ES+): 375 (M+H)+. added to a separation funnel partitioned with sodium bicarbonate (saturated, aqueous) washed 2× with 50 mL of sodium bicarbonate (saturated, aqueous) separated dried over sodium sulfate concentrated in vacuo purified by HPLC

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3-Iodobenzoic acid (4.79 g, 19.3 mmol) was suspended in thionyl chloride (19.3 mL) and stirred for 1 h at 70° C. before it was conc. and azeotropically dried with toluene. The reaction mixture was dissolved in dioxane (19.3 mL) before N-ethyl-N-isopropylpropan-2-amine (13.5 mL, 77.3 mmol) and cyclopropylamine (6.77 mL, 96.6 mmol) were added and stirred for 16 h at ambient temperature. The reaction mixture was diluted with 75 mL of ethyl acetate, added to a separation funnel, partitioned with sodium bicarbonate (saturated, aqueous), washed 2× with 50 mL of 3 N HCl (aqueous), separated, dried over sodium sulfate, and concentrated in vacuo to give the title compound. MS (ES+): 288 (M+H)+. azeotropically dried with toluene were added stirred for 16 h at ambient temperature added to a separation funnel partitioned with sodium bicarbonate (saturated, aqueous) washed 2× with 50 mL of 3 N HCl (aqueous) separated dried over sodium sulfate concentrated in vacuo

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3-Iodobenzoic acid (4.79 g, 19.3 mmol) was suspended in thionyl chloride (19.3 mL) and stirred for 1 h at 70° C. before it was conc. and azeotropically dried with toluene. The reaction mixture was dissolved in dioxane (19.3 mL) before N-ethyl-N-isopropylpropan-2-amine (13.5 mL, 77.3 mmol) and cyclopropylamine (6.77 mL, 96.6 mmol) were added and stirred for 16 h at ambient temperature. The reaction mixture was diluted with 75 mL of ethyl acetate, added to a separation funnel, partitioned with sodium bicarbonate (saturated, aqueous), washed 2× with 50 mL of 3 N HCl (aqueous), separated, dried over sodium sulfate, and concentrated in vacuo to give the title compound. MS (ES+): 288 (M+H)+. azeotropically dried with toluene were added stirred for 16 h at ambient temperature added to a separation funnel partitioned with sodium bicarbonate (saturated, aqueous) washed 2× with 50 mL of 3 N HCl (aqueous) separated dried over sodium sulfate concentrated in vacuo