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Chemical Structure| 1417885-96-1 Chemical Structure| 1417885-96-1

Structure of 1417885-96-1

Chemical Structure| 1417885-96-1

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Product Details of [ 1417885-96-1 ]

CAS No. :1417885-96-1
Formula : C9H5BrF3N3O
M.W : 308.05
SMILES Code : FC(F)(F)OC1=CC=C(N2N=C(Br)N=C2)C=C1
MDL No. :MFCD30731618

Safety of [ 1417885-96-1 ]

Application In Synthesis of [ 1417885-96-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1417885-96-1 ]

[ 1417885-96-1 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 7343-33-1 ]
  • [ 103962-05-6 ]
  • [ 1417885-96-1 ]
YieldReaction ConditionsOperation in experiment
73% With copper(l) iodide; caesium carbonate; In dimethyl sulfoxide; at 100℃; for 36h;Inert atmosphere; A dry round bottom flask was charged with <strong>[7343-33-1]3-bromo-1H-1,2,4-triazole</strong> (5 g, 33.8 mmol), CuI (0.644 g, 3.38 mmol), and Cs2CO3 (11.01 g, 33.8 mmol). The flask was evacuated/backfilled with N2, then DMSO (33.8 mL) and 1-iodo-4-(trifluoromethoxy)benzene (4.87 g, 16.90 mmol) were added. The reaction mixture was heated to 100° C. for 36 h. The reaction mixture was cooled to room temperature, diluted with EtOAc, filtered through a plug of Celite® and further washed with EtOAc. Water was added to the combined organics, and the layers were separated. The aqueous phase was neutralized to pH 7, and further extracted with EtOAc. The combined organics were concentrated in vacuo. Purification via flash chromatography (silica/EtOAc/Hexanes) yielded 3-bromo-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole as an off white solid (3.78 g, 73percent yield): mp 67-69° C.; 1H NMR (400 MHz, CDCl3) delta 8.43 (s, 1H), 7.70 (m, 2H), 7.38 (m, 2H); 19F NMR (376 MHz, CDCl3) delta -58.02.
73% With copper(l) iodide; caesium carbonate; In dimethyl sulfoxide; at 100℃; for 20h;Inert atmosphere; To a 250 mL reaction flask was added <strong>[7343-33-1]3-bromo-1H-1,2,4-triazole</strong> (5 g, 33.8 mmol), CuI (0.644 g, 3.38 mmol) and Cs2CO3 (11.01 g, 33.8 mmol). The flask was evacuated/backfilled with nitrogen gas, and then DMSO (33.8 ml) and 1-iodo-4-(trifluoromethoxy)benzene (4.87 g, 16.90 mmol) were added. The reaction mixture was heated to 100° C. for 20 hours (h). The reaction was cooled to room temperature, diluted with EtOAc and filtered through a plug of Celite®. The Celite® was further washed with EtOAc. Water was added to the combined organics, and the layers were separated. The aqueous phase was neutralized to pH 7, and further extracted with EtOAc. The combined organics were concentrated in vacuo. Purification via flash column chromatography using EtOAc/hexanes as eluent to yield the title compound (3.78 g, 73percent): mp 69-70° C.; 1H NMR (400 MHz, CDCl3) delta 8.44 (s, 1H), 7.70 (d, J=8.9 Hz, 2H), 7.38 (d, J=8.5 Hz, 2H); 19F NMR (376 MHz, CDCl3) delta ?58.04; EIMS m/z 307 ([M]+).
73% With copper(l) iodide; caesium carbonate; In dimethyl sulfoxide; at 100℃; for 20h;Inert atmosphere; To a 250 mL reaction flask was added <strong>[7343-33-1]3-bromo-1H-1,2,4-triazole</strong> (5 g, 33.8 mmol), CuI (0.644 g, 3.38 mmol) and Cs2CO3 (11.01 g, 33.8 mmol). The flask was evacuated/backfilled with nitrogen gas, and then DMSO (33.8 ml) and 1-iodo-4-(trifluoromethoxy)benzene (4.87 g, 16.90 mmol) were added. The reaction mixture was heated to 100° C. for 20 hours (h). The reaction wascooled to room temperature (RT), diluted with EtOAc and filtered through a plug of Celite®. The Celite® was further washed with EtOAc. Water was added to the combined organics, and the layers were separated. The aqueous phase was neutralized to pH 7, and further extracted with EtOAc. The combined organics were concentrated in vacuo. Purification via flash column chromatography using EtOAc/hexanes as eluent provided the title compound as an off-white solid (3.78 g, 73percent): mp 69-70° C.; 1H NMR (400 MHz, CDCl3) delta 8.44 (s, 1H), 7.70 (d, J=8.9 Hz, 2H), 7.38 (d, J=8.5 Hz, 2H); 19F NMR (376 MHz, CDCl3) delta-58.04; EIMS m/z 307 ([M]+)
72.6% With copper(l) iodide; caesium carbonate; In dimethyl sulfoxide; at 100℃; for 20h;Inert atmosphere; Example 59. Preparation of 3-bromo-l-(4-(trifluoromethoxy)phenyl)-lH-l,2,4-triazole (B61) To a 250 mL reaction flask was added 3-bromo-lH-l,2,4-triazole (5 g, 33.8 mmol), copper(I) iodide (0.644 g, 3.38 mmol) and cesium carbonate (11.01 g, 33.8 mmol). The flask was evacuated/backfilled with N2, then DMSO (33.8 ml) and l-iodo-4-(trifluoromethoxy)benzene (4.87 g, 16.90 mmol) were added. The reaction mixture was heated to 100 °C for 20 h. The reaction was cooled to room temperature, diluted with EtOAc and filtered through a plug of Celite. The Celite was further washed with EtOAc. Water was added to the combined organics, and the layers were separated. The aqueous phase was neutralized to pH 7, and further extracted with EtOAc. The combined organics were concentrated in vacuo. Purification via flash chromatography (silica/EtO Ac/Hex) yielded 3-bromo-l-(4- (trifluoromethoxy)phenyl)-lH-l,2,4-triazole as an off white solid (3.78 g, 12.27 mmol, 72.6percent): mp 69-70 °C; ]H NMR (400 MHz, CDC13) delta 8.44 (s, 1H), 7.70 (d, / = 8.9 Hz, 2H), 7.38 (d, J = 8.5 Hz, 2H); 19F NMR (376 MHz, CDC13) delta -58.04; EIMS m/z 307.
72.6% With copper(l) iodide; caesium carbonate; In dimethyl sulfoxide; at 100℃; for 20h;Inert atmosphere; To a 250 mL reaction flask was added <strong>[7343-33-1]3-bromo-1H-1,2,4-triazole</strong> (5 g, 33.8 mmol), CuI (0.644 g, 3.38 mmol) and Cs2CO3 (11.01 g, 33.8 mmol). The flask was evacuated/backfilled with nitrogen gas, and then DMSO (33.8 ml) and 1-iodo-4-(trifluoromethoxy)benzene (4.87 g, 16.90 mmol) were added. The reaction mixture was heated to 100° C. for 20 hours (h). The reaction was cooled to room temperature (RT), diluted with EtOAc and filtered through a plug of Celite®. The Celite® was further washed with EtOAc. Water was added to the combined organics, and the layers were separated. The aqueous phase was neutralized to pH 7, and further extracted with EtOAc. The combined organics were concentrated in vacuo. Purification via flash chromatography (silica/EtOAc/hexanes) yielded 3-bromo-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole as an off-white solid (3.78 g, 12.27 mmol, 72.6percent): mp 69-70° C.; 1H NMR (400 MHz, CDCl3) delta 8.44 (s, 1H), 7.70 (d, J=8.9 Hz, 2H), 7.38 (d, J=8.5 Hz, 2H); 19F NMR (376 MHz, CDCl3) delta ?58.04; EIMS m/z 307.
72.6% With copper(l) iodide; caesium carbonate; In dimethyl sulfoxide; at 100℃; for 36h;Inert atmosphere; Example 6 Preparation of 3-bromo-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole A dry round bottom flask was charged with <strong>[7343-33-1]3-bromo-1H-1,2,4-triazole</strong> (5 g, 33.8 mmol), CuI (0.644 g, 3.38 mmol), and Cs2CO3 (11.01 g, 33.8 mmol). The flask was evacuated/backfilled with N2, then DMSO (33.8 mL) and 1-iodo-4-(trifluoromethoxy)benzene (4.87 g, 16.90 mmol) were added. The reaction mixture was heated to 100° C. for 36 h. The reaction mixture was cooled to room temperature, diluted with EtOAc, filtered through a plug of Celite® and further washed with EtOAc. Water was added to the combined organics, and the layers were separated. The aqueous phase was neutralized to pH 7, and further extracted with EtOAc. The combined organics were concentrated in vacuo. Purification via flash column chromatography (EtOAc/hexanes) yielded the title compound as an off white solid (3.78 g, 72.6percent): mp 67-69° C.; 1H NMR (400 MHz, CDCl3) delta 8.43 (s, 1H), 7.70 (m, 2H), 7.38 (m, 2H); 19F NMR (376 MHz, CDCl3) delta -58.02. Example 5 Preparation of 3-bromo-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole A dry round bottom flask was charged with potassium phosphate (K3PO4, 7.74 g, 36.5 mmol), CuI (0.165 g, 0.868 mmol), and <strong>[7343-33-1]3-bromo-1H-1,2,4-triazole</strong> (2.83 g, 19.10 mmol). The flask was evacuated/backfilled with N2 (3*). DMF (34.7 mL) was added, followed by trans-(1R,2R)-N,N'-bismethyl-1,2-cyclohexane diamine (0.274 ml, 1.736 mmol) and 1-iodo-4-(trifluoromethoxy)benzene (5.000 g, 17.36 mmol). The solution was heated to 110° C. After 48 h, the reaction mixture was cooled to room temperature, diluted with EtOAc and filtered through Celite®. The filtrate was washed with water (100 mL) containing HCl (1 M, 10 mL. The organics were separated, and the aqueous phase was further extracted with EtOAc (3*). The organics were combined, dried, and concentrated in vacuo. Purification via flash column chromatography (EtOAc/hexanes) yielded the title compound as a tan solid (1.86 g, 34percent): 1H NMR (400 MHz, CDCl3) delta 8.44 (s, 1H), 7.70 (d, J=8.9 Hz, 2H), 7.38 (d, J=8.5 Hz, 2H); 19F NMR (376 MHz, CDCl3) delta -58.04; EIMS m/z 307.
54% With copper(l) iodide; caesium carbonate; In dimethyl sulfoxide; at 100℃; for 20h;Inert atmosphere; To a 100 mL round bottomed flask, equipped with a stir bar, was added copper(I) iodide (0.397 g, 2.08 mmol), <strong>[7343-33-1]3-bromo-1H-1,2,4-triazole</strong> (4.62 g, 31.2 mmol), and cesium carbonate (6.79 g, 20.83 mmol), as solids. These solids were diluted with anhydrous dimethyl sulfoxide (34.7 mL). Then 1-iodo-4-(trifluoromethoxy)benzene (1.65 mL, 10.4 mmol) was added as a liquid. The flask was placed under nitrogen atmosphere, and the suspension was heated to an internal temperature of 100° C. for 20 hours. The reaction mixture was allowed to cool to room temperature and filtered through a pad of Celite®, washing with excess ethyl acetate (200 mL). The filtrate was poured into a brine solution (200 mL), and the layers were partitioned. The aqueous phase was extracted with additional ethyl acetate (2*100 mL). The combined organic layers were dried over anhydrous magnesium sulfate, filtered, and concentrated. The resulting residue was purified via flash column chromatography using 10-50percent ethyl acetate/hexanes as eluent to afford the title compound as a white solid (1.80 g, 54percent): 1H NMR (400 MHz, DMSO-d6) delta 9.35 (s, 1H), 7.97 (d, J=8.9 Hz, 2H), 7.60 (d, J=8.4 Hz, 2H); 19F NMR (376 MHz, DMSO-d6) delta -57.06; ESIMS m/z 308, 310 ([M+H]+).
34% With copper(l) iodide; (R,R)-N,N'-dimethyl-1,2-diaminocyclohexane; In N,N-dimethyl-formamide; at 110℃; for 48h;Inert atmosphere; A dry round bottom flask was charged with potassium phosphate (K3PO4, 7.74 g, 36.5 mmol), CuI (0.165 g, 0.868 mmol), and <strong>[7343-33-1]3-bromo-1H-1,2,4-triazole</strong> (2.83 g, 19.10 mmol). The flask was evacuated/backfilled with N2 (3*). DMF (34.7 ml) was added, followed by trans-(1R,2R)-N,N'-bismethyl-1,2-cyclohexane diamine (0.274 ml, 1.736 mmol) and 1-iodo-4-(trifluoromethoxy)benzene (5 g, 17.36 mmol). The solution was heated to 110° C. After 48 h, the reaction mixture was cooled to RT, diluted with EtOAc and filtered through Celite®. The filtrate was washed with water (100 mL) containing 10 mL 1 M HCl. The organics were separated, and the aqueous phase was further extracted with EtOAc (3*). The organics were combined, dried, and concentrated in vacuo. Purification via flash column chromatography (EtOAc/hexanes) yielded the title compound as a tan solid (1.86 g, 34percent): 1H NMR (400 MHz, CDCl3) delta 8.44 (s, 1H), 7.70 (d, J=8.9 Hz, 2H), 7.38 (d, J=8.5 Hz, 2H); 19F NMR (376 MHz, CDCl3) delta -58.04; EIMS m/z 307 ([M]+).
With copper(l) iodide; caesium carbonate; In dimethyl sulfoxide; at 100℃; for 20h;Inert atmosphere; To a 250 mL reaction flask was added 3-bromo-lH-l,2,4-triazole (5 g, 33.8 mmol), copper(I) iodide (0.644 g, 3.38 mmol) and cesium carbonate (11.01 g, 33.8 mmol). The flask was evacuated/backfilled with N2, then DMSO (33.8 ml) and l-iodo-4-(trifluoromethoxy)benzene (4.87 g, 16.90 mmol) were added. The reaction mixture was heated to 100 °C for 20 h. The reaction was cooled to room temperature, diluted with EtOAc and filtered through a plug of Celite. The Celite was further washed with EtOAc. Water was added to the combined organics, and the layers were separated. The aqueous phase was neutralized to pH 7, and further extracted with EtOAc. The combined organics were concentrated in vacuo.Purification via flash chromatography (silica/EtO Ac/Hex) yielded 3-bromo-l-(4- (trifluoromethoxy)phenyl)-lH-l,2,4-triazole as an off white solid (3.78 g, 12.27 mmol,72.6percent): mp 69-70 °C; ]H NMR (400 MHz, CDC13) delta 8.44 (s, 1H), 7.70 (d, / = 8.9 Hz, 2H), 7.38 (d, J = 8.5 Hz, 2H); 19F NMR (376 MHz, CDC13) delta -58.04; EIMS m/z 307.
With caesium carbonate; In water; dimethyl sulfoxide; Example 6 Preparation of 3-bromo-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole A dry round bottom flask was charged with <strong>[7343-33-1]3-bromo-1H-1,2,4-triazole</strong> (5 g, 33.8 mmol), CuI (0.644 g, 3.38 mmol), and Cs2CO3 (11.01 g, 33.8 mmol). The flask was evacuated/backfilled with N2, then DMSO (33.8 mL) and 1-iodo-4-(trifluoromethoxy)benzene (4.87 g, 16.90 mmol) were added. The reaction mixture was heated to 100° C. for 36 h. The reaction mixture was cooled to RT, diluted with EtOAc, filtered through a plug of Celite® and further washed with EtOAc. Water was added to the combined organics, and the layers were separated. The aqueous phase was neutralized to pH 7, and further extracted with EtOAc. The combined organics were concentrated in vacuo. Purification via flash column chromatography EtOAc/hexanes yielded the title compound as an off white solid (3.78 g, 73percent): mp 67-69° C.; 1H NMR (400 MHz, CDCl3) delta 8.43 (s, 1H), 7.70 (m, 2H), 7.38 (m, 2H); 19F NMR (376 MHz, CDCl3) delta-58.02.
With caesium carbonate; In water; dimethyl sulfoxide; Example 6 Preparation of 3-bromo-1-(4-(trifluoromethoxy)Phenyl)-1H-1,2,4-triazole A dry round bottom flask was charged with <strong>[7343-33-1]3-bromo-1H-1,2,4-triazole</strong> (5 g, 33.8 mmol), CuI (0.644 g, 3.38 mmol), and Cs2CO3 (11.01 g, 33.8 mmol). The flask was evacuated/backfilled with N2, then DMSO (33.8 mL) and 1-iodo-4-(trifluoromethoxy)benzene (4.87 g, 16.90 mmol) were added. The reaction mixture was heated to 100° C. for 36 h. The reaction mixture was cooled to RT, diluted with EtOAc, filtered through a plug of Celite® and further washed with EtOAc. Water was added to the combined organics, and the layers were separated. The aqueous phase was neutralized to pH 7, and further extracted with EtOAc. The combined organics were concentrated in vacuo. Purification via flash column chromatography (EtOAc/Hexanes) yielded the title compound as an off white solid (3.78 g, 73percent): mp 67-69° C.; 1H NMR (400 MHz, CDCl3) delta 8.43 (s, 1H), 7.70 (m, 2H), 7.38 (m, 2H); 19F NMR (376 MHz, CDCl3) delta -58.02.
3 g With copper(l) iodide; caesium carbonate; In dimethyl sulfoxide; at 130℃; for 18h;Inert atmosphere; Sealed tube; To a mixture of 1 -iodo-4-(trifluoromethoxy)benzene (3 g, 10.416 mmol) in methylsulfinylmethane (24 mL) was added 3-bromo-1 H-1 ,2,4-triazole (3.1 g) under nitrogen atmosphere followed by addition of cesium carbonate (6.7 g, 20.833 mmol) and copper iodide (0.4 g, 2.083 mmol). The reaction mass was stirred at 130°C for 18 hours in seal tube. The reaction mass was then diluted with water and extracted with ethylacetate (3 x 70 mL). The combined organic layers were then dried over sodium sulphate and concentrated under reduced pressure followed by column chromatography to obtain the title compound as solid (3 g). (0581) H NMR (400 MHz, (CD3)3SO): delta 9.38 - 9.25 (m, 1 H), 7.98 - 7.92 (m, 2H), 7.65 - 7.53 (m, 2H) LC/MS (method E) m/z: 308 [M + H]+, Rt = 0.94 min.

  • 2
  • [ 525362-07-6 ]
  • [ 1417885-96-1 ]
  • [ 1417885-97-2 ]
YieldReaction ConditionsOperation in experiment
62% With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate; In 1,4-dioxane; water; at 140℃; for 0.5h;Microwave irradiation; To 3-bromo-l-(4-(trifluoromethoxy)phenyl)-lH-l,2,4-triazole (0.496 g, 1.609 mmol), methyl 2-methyl-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)benzoate (0.466 g, 1.689 mmol), sodium bicarbonate (0.405 g, 4.83 mmol) and tetrakis(triphenylphosphine)palladium (0.186 g, 0.161 mmol) in a 2.0 mL microwave vial was added dioxane (6 mL) and water (1.5 mL). The reaction was capped and placed on a Biotage Initiator microwave reactor for 30 min at 140 C. The reaction mixture was then diluted with EtOAc and washed with water. The aqueous layer was extracted with EtOAc. The combined organic layers were dried over MgS04, filtered and concentrated. Purification by flash column chromatography provided the title compound as a white solid (0.376 g, 0.997 mmol, 62%): ]H NMR (400 MHz, CDC13) δ 8.59 (s, 1H), 8.10 (dt, / = 1.6, 0.7 Hz, 1H), 8.09 - 8.00 (m, 2H), 7.84 - 7.78 (m, 2H), 7.44 - 7.37 (m, 2H), 3.93 (s, 3H), 2.70 (s, 3H); 19F NMR (376 MHz, CDC13) δ -58.02; ESIMS m/z 378 ([M+H]+)
62% With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate; In 1,4-dioxane; water; at 140℃; for 0.5h;Microwave irradiation; Example 60. Preparation of methyl 2-methyl-4-(l-(4-(trifluoromethoxy)phenyl)-lH- l,2,4-triazol-3-yl) benzoate To 3-bromo-l-(4-(trifluoromethoxy)phenyl)-lH-l,2,4-triazole (0.496 g, 1.609 mmol), methyl 2-methyl-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)benzoate (0.466 g, 1.689 mmol), sodium bicarbonate (0.405 g, 4.83 mmol) and tetrakis(triphenylphosphine)palladium (0.186 g, 0.161 mmol) in a 2.0 mL microwave vial was added dioxane (6 mL) and water (1.5 mL). The reaction was capped and placed on a Biotage Initiator microwave reactor for 30 min at 140 C. The reaction mixture was then diluted with EtOAc and washed with water. The aqueous layer was extracted with EtOAc. The combined organic layers were dried over MgS04, filtered and concentrated. Purification by flash column chromatography provided the title compound as a white solid (0.376 g, 0.997 mmol, 62%): ]H NMR (400 MHz, CDC13) δ 8.59 (s, 1H), 8.10 (dt, / = 1.6, 0.7 Hz, 1H), 8.09 - 8.00 (m, 2H), 7.84 - 7.78 (m, 2H), 7.44 - 7.37 (m, 2H), 3.93 (s, 3H), 2.70 (s, 3H); 19F NMR (376 MHz, CDC13) δ -58.02; ESIMS m/z 378 ([M+H]+).
  • 3
  • [ 7343-33-1 ]
  • potassium phosphate [ No CAS ]
  • [ 68737-65-5 ]
  • [ 103962-05-6 ]
  • [ 1417885-96-1 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In N,N-dimethyl-formamide; Example 5 Preparation of 3-bromo-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole A dry round bottom flask was charged with potassium phosphate (K3PO4, 7.74 g, 36.5 mmol), CuI (0.165 g, 0.868 mmol), and <strong>[7343-33-1]3-bromo-1H-1,2,4-triazole</strong> (2.83 g, 19.10 mmol). The flask was evacuated/backfilled with N2 (3*). DMF (34.7 ml) was added, followed by trans-(1R,2R)-N,N'-bismethyl-1,2-cyclohexane diamine (0.274 ml, 1.736 mmol) and 1-iodo-4-(trifluoromethoxy)benzene (5 g, 17.36 mmol). The solution was heated to 110° C. After 48 h, the reaction mixture was cooled to RT, diluted with EtOAc and filtered through Celite®. The filtrate was washed with water (100 mL) containing HCl (1 M, 10 mL). The organics were separated, and the aqueous phase was further extracted with EtOAc (3*). The organics were combined, dried, and concentrated in vacuo. Purification via flash column chromatography EtOAc/hexanes yielded the title compound as a tan solid (1.86 g, 34percent): 1H NMR (400 MHz, CDCl3) delta 8.44 (s, 1H), 7.70 (d, J=8.9 Hz, 2H), 7.38 (d, J=8.5 Hz, 2H); 19F NMR (376 MHz, CDCl3) delta-58.04; EIMS m/z 307 ([M]+).
With hydrogenchloride; In N,N-dimethyl-formamide; Example 5 Preparation of 3-bromo-1-(4-(trifluoromethoxy)Phenyl)-1H-1,2,4-triazole A dry round bottom flask was charged with potassium phosphate (K3PO4, 7.74 g, 36.5 mmol), CuI (0.165 g, 0.868 mmol), and <strong>[7343-33-1]3-bromo-1H-1,2,4-triazole</strong> (2.83 g, 19.10 mmol). The flask was evacuated/backfilled with N2 (3*). DMF (34.7 mL) was added, followed by trans-(1R,2R)-N,N'-bismethyl-1,2-cyclohexane diamine (0.274 mL, 1.736 mmol) and 1-iodo-4-(trifluoromethoxy)benzene (5 g, 17.36 mmol). The solution was heated to 110° C. After 48 h, the reaction mixture was cooled to RT, diluted with EtOAc and filtered through Celite®. The filtrate was washed with water (100 mL) containing HCl (1 M, 10 mL). The organics were separated, and the aqueous phase was further extracted with EtOAc (3*). The organics were combined, dried with sodium sulfate, and concentrated in vacuo. Purification via flash column chromatography (EtOAc/hexanes) yielded the title compound as a tan solid (1.86 g, 34percent): 1H NMR (400 MHz, CDCl3) delta 8.44 (s, 1H), 7.70 (d, J=8.9 Hz, 2H), 7.38 (d, J=8.5 Hz, 2H); 19F NMR (376 MHz, CDCl3) delta-58.04; EIMS m/z 307 ([M]+).
  • 4
  • [ 1417885-96-1 ]
  • [ 3375-31-3 ]
  • [ 131274-22-1 ]
  • [ 454185-98-9 ]
  • methyl 2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 33 Preparation of methyl 2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)acetate (C17) In a 200 mL flask, 3-bromo-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole (3.45 g, 11.2 mmol), and methyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate (3.71 g, 13.4 mmol) were diluted with dioxane (45 mL) and water (11 mL). This solution was sparged with nitrogen gas for 10 minutes. Then tri-tert-butylphosphonium tetrafluoroborate (0.325 g, 1.12 mmol), diacetoxypalladium (0.126 g, 0.560 mmol) and cesium fluoride (3.40 g, 22.4 mmol) were added as solids. The flask was sealed and evacuated with vacuum and purged with nitrogen gas. The reaction was warmed to an internal temperature of 60° C. and stirred for 18 hours. The reaction was poured into a brine solution and extracted with ethyl acetate (3*50 mL). The combined organics were dried over magnesium sulfate, filtered, and concentrated. The resulting residue was purified by flash chromatography using 0-10percent ethyl acetate/hexanes as eluent to afford the title compound as an off white solid (3.45 g, 82percent): 1H NMR (400 MHz, DMSO-d6) delta 9.41 (s, 1H), 8.11-8.04 (m, 4H), 7.63 (ddt, J=7.9, 2.1, 1.1 Hz, 2H), 7.48-7.36 (m, 2H), 3.77 (s, 2H), 3.64 (s, 3H); 19F NMR (376 MHz, DMSO-d6) delta -57.02; ESIMS m/z 378 ([M+H]+)
 

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