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Chemical Structure| 866638-72-4
Chemical Structure| 866638-72-4
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Product Details of [ 866638-72-4 ]

CAS No. :866638-72-4 MDL No. :MFCD08064883
Formula : C4H2F3IN2 Boiling Point : -
Linear Structure Formula :- InChI Key :XRUHSOXIZMYOHX-UHFFFAOYSA-N
M.W : 261.97 Pubchem ID :16069792
Synonyms :

Safety of [ 866638-72-4 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P301+P310 UN#:2811
Hazard Statements:H301 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 866638-72-4 ]

* 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 [ 866638-72-4 ]

[ 866638-72-4 ] Synthesis Path-Downstream   1~24

  • 1
  • [ 866638-72-4 ]
  • [ 18515-14-5 ]
  • [ 866638-73-5 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 60℃; for 1h; 14 3-Methyl-4-nitrobenzyl chloride (0.77 g), 4-iodo-3-trifluoromethyl-lH-pyrazole (0.99 g) and potas- sium carbonate (0.63 g) were stirred in DMF (10 ml) at 60 C for 1 hour. After cooling, the reaction solution was diluted with ethyl acetate and washed with water and saturated aqueous solution of sodium chloride. After drying the organic layer with magnesium sulfate, the solvent was distilled off under the reduced pressure and the obtained residue was purified by silica gel column chromato- graphy to obtain 4-iodo-1- (3-methyl-4-nitrobenzyl)-3-tifluoromethyl-lH-pyrazole (1.0 g). 'H-NMR (CDC13, ppm): 2.62 (3H, s), 5.36 (2H, s), 7.21-7. 18 (2H, m), 7.52 (1H, s), 7.98 (1H, d).
  • 2
  • [ 20154-03-4 ]
  • [ 866638-72-4 ]
YieldReaction ConditionsOperation in experiment
88.17% With N-iodo-succinimide; sulfuric acid In lithium hydroxide monohydrate at 0 - 20℃; for 13.1667h; 499.3 Step 3: 4-iodo-3-(trifluoromethyl)-1H-pyrazole To a solution of 3-(trifluoromethyl)pyrazole (74 g, 543.8 mmol) in aqueous sulfuric acid (160 mL, 543.8 mmol) was added N-iodosuccinimide (146.81 g, 652.56 mmol) at 0 °C and it was stirred for 10 min. Then it was warmed to 20 °C and stirred for 1 h. Water (2 L) was added to the mixture and it was stirred at 20 °C for 12 h. The reaction mixture was filtered. The filter cake was dissolved in EtOAc (1.5 L) and washed with saturated Na2SO3 (1 L). The organic layer was washed with brine (1 L), dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography (SiO2, PE:EtOAc=3:1) to yield the title compound as a white solid (125.6 g, 479.44 mmol, 88.17% yield). MS(m/e): 262.9 (M+H).
88.17% With N-iodo-succinimide; sulfuric acid In lithium hydroxide monohydrate at 0 - 20℃; for 13.1667h; 499.3 Step 3: 4-iodo-3-(trifluoromethyl)-1H-pyrazole To a solution of 3-(trifluoromethyl)pyrazole (74 g, 543.8 mmol) in aqueous sulfuric acid (160 mL, 543.8 mmol) was added N-iodosuccinimide (146.81 g, 652.56 mmol) at 0 °C and it was stirred for 10 min. Then it was warmed to 20 °C and stirred for 1 h. Water (2 L) was added to the mixture and it was stirred at 20 °C for 12 h. The reaction mixture was filtered. The filter cake was dissolved in EtOAc (1.5 L) and washed with saturated Na2SO3 (1 L). The organic layer was washed with brine (1 L), dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography (SiO2, PE:EtOAc=3:1) to yield the title compound as a white solid (125.6 g, 479.44 mmol, 88.17% yield). MS(m/e): 262.9 (M+H).
86.49% With N-iodo-succinimide; sulfuric acid In dichloromethane at 0 - 20℃; for 3.16667h; Inert atmosphere; 8.1 4-Iodo-3-(trifluoromethyl)-1H-pyrazole A solution of 3-(trifluoromethyl)pyrazole (200.0 g, 1470 mmol, 1 eq) in sulfuric acid (100.0 mL, 1470 mmol, 1 eq)/water (400 mL) was added N-iodosuccinimide (396.79 g, 1764 mmol, 1.2 eq) at 0°C and stirred for 10 min, then the solution was stirred at 20°C for 3h. Then the mixture was poured into water (3 L) and stirred for another 13h. The mixture was filtered and to the residue was added saturated Na2SO3 solution (1000 mL) , extracted with EtOAc (1000 mL*2), washed with brine (1000 mL), dried to afford the title compound (333 g, 1271 mmol, 86.49% yield) as white solid. MS (ESI, m/z): 262.8 [M+H]+
86.49% With N-iodo-succinimide; sulfuric acid In dichloromethane at 0 - 20℃; for 3.16667h; Inert atmosphere; 8.1 4-Iodo-3-(trifluoromethyl)-1H-pyrazole A solution of 3-(trifluoromethyl)pyrazole (200.0 g, 1470 mmol, 1 eq) in sulfuric acid (100.0 mL, 1470 mmol, 1 eq)/water (400 mL) was added N-iodosuccinimide (396.79 g, 1764 mmol, 1.2 eq) at 0°C and stirred for 10 min, then the solution was stirred at 20°C for 3h. Then the mixture was poured into water (3 L) and stirred for another 13h. The mixture was filtered and to the residue was added saturated Na2SO3 solution (1000 mL) , extracted with EtOAc (1000 mL*2), washed with brine (1000 mL), dried to afford the title compound (333 g, 1271 mmol, 86.49% yield) as white solid. MS (ESI, m/z): 262.8 [M+H]+
85% With N-iodo-succinimide; sulfuric acid In lithium hydroxide monohydrate at 0℃; for 3.16667h; regioselective reaction; 2.5. Iodination of compound 1e and 1f General procedure: The considered 3-trifluoromethylpyrazole (68 mmol) was dissolved in 50% aqueous sulfuric acid (20 mL). This was cooled to 0 °C and N-iodosuccinimide (18.5 g, 82 mmol) was added. The suspension was stirred 10 min at 0 °C and then stirred, 3 h for 1e and two days for 1f, at room temperature. This was dispersed in water (500 mL) and stirred overnight. The precipitate was filtered, washed with water and redispersed in boiling water (400 mL), a small amount of sodium disulfite was added and the suspension was left to cool, filtered again and dried under vacuum to yield compound 2e or 2f as described below.
73% With N-iodo-succinimide; sulfuric acid In lithium hydroxide monohydrate at 0 - 20℃; for 3h; 508.1 Step 1. Synthesis of 4-iodo-3- (trifluoromethyl) -1H-pyrazole To a solution of 3- (trifluoromethyl) -1H-pyrazole (1.0 g, 7 mmol) in H 2SO 4 (15 mL) was added NIS (1.65 g, 7.3 mmol) at 0 °C. After the reaction mixture was stirred at rt for 3 h, it was diluted with water. After filtration, the filter cake was dried to provide the title compound (1.4 g, yield: 73%) as white solid. MS (ESI) m/z = 262.9 [M+H] +.
73% With N-iodo-succinimide; sulfuric acid In lithium hydroxide monohydrate at 0 - 20℃; for 3h; 508.1 Step 1. Synthesis of 4-iodo-3- (trifluoromethyl) -1H-pyrazole To a solution of 3- (trifluoromethyl) -1H-pyrazole (1.0 g, 7 mmol) in H 2SO 4 (15 mL) was added NIS (1.65 g, 7.3 mmol) at 0 °C. After the reaction mixture was stirred at rt for 3 h, it was diluted with water. After filtration, the filter cake was dried to provide the title compound (1.4 g, yield: 73%) as white solid. MS (ESI) m/z = 262.9 [M+H] +.
69% With N-iodo-succinimide; sulfuric acid at 15℃; for 3h; Inert atmosphere; 77 Example 77: Synthesis of 4-iodo-3-(trifluoromethyl)-1H-pyrazole (101) To a solution of 100 (30.0 g, 147.0 mmol) in H2SO4 (600 mL, 50%) was added N-iodosuccinimide (39.7 g, 176.4 mmol). The mixture was stirred at 15° C. for 3 h. The reaction was diluted with H2O (800 mL) and stirred at 15° C. for another 12 h. The mixture was filtered and the filter cake was washed with H2O (3×300 mL), then concentrated in vacuum to obtain 101 (40.0 g, 69% yield, 99% purity) as white solid. [M+H]+ calcd for C4H2F3IN2 262.92, found 262.8
With dicerium ammonium nitrate; iodine In acetonitrile for 1h; Heating / reflux; 13 An acetonitrile solution (30 ml) of 3-trifluoromethyl-lH-pyrazole (5.0 g), dicerium ammonium nitrate (10.0 g) and iodine (5.6 g) was refluxed for 1 hour. After cooling, the reaction solution was washed with saturated aqueous solution of sodium thiosulfate and saturated aqueous solution of sodium chloride. After drying the organic layer with magnesium sulfate, the solvent was distilled off under the reduced pressure to obtain 4-iodo-3-trifluoromethyl-lH-pyrazole (9. 3 g). 'H-NMR (CDC13, ppm): 7.77 (1H, s).
With N-iodo-succinimide; sulfuric acid In lithium hydroxide monohydrate at 0 - 20℃; for 3.16667h; 31.1 Step 1: Preparation of 4-iodo-3-(trifluoromethyl)-1H-pyrazole Step 1: Preparation of 4-iodo-3-(trifluoromethyl)-1H-pyrazole To a solution of 3-(trifluoromethyl)-1H-pyrazole (500 mg, 3.7 mmol) in 50% H2SO4 at 0° C. was added NIS (992 mg, 4.4 mmol). The suspension was stirred at 0° C. for 10 min and then at r.t. for 3 hr. The resulting mixture was quenched with water (50 mL), and then stirred overnight. The precipitate was collected by filtration and dried to afford 4-iodo-3-(trifluoromethyl)-1H-pyrazole. LC-MS: m/z 263 (M+H)+.
With N-iodo-succinimide; sulfuric acid at 0 - 20℃; for 3.16667h; 31.1 Step 1: Preparation of 4-iodo-3-(truoromethyl)-1H-pyrazole. Step 1: Preparation of 4-iodo-3-(truoromethyl)-1H-pyrazole. To a solution of 3- (trifluoromethyl)-1H-pyrazole (500 mg, 3.7 mmol) in 50% 112S04 at 0 °C was added MS (992 mg, 4.4 mmol). The suspension was stirred at 0°C for 10 mm and then at r.t. for 3 hr. The resulting mixture was quenched with water (50 mL), and then stirred overnight. The precipitate was collected by filtration and dried to afford 4-iodo-3-(trifluoromethyl)-1H-pyrazole.LC-MS:m/z 263 (M+H).
With N-iodo-succinimide In N,N-dimethyl-formamide at 20℃; for 16h; 4-chloro-3-iodo-1H-pyrrolo[2,3-b]pyridine (13) General procedure: A solution of 4-chloro-7-azaindole (2.00 g, 13.1 mmol) and N-iodo succinimide (2.95 g, 13.1 mmol) in DMF (15 mL) was stirred at rt overnight. The mixture was partitioned between EtOAc and sat. aq. NaHCO3, and the organic layer was concentrated and dried under vacuum to provide compound 13 (3.65 g, 13.1 mmol) in quantitative yield. Found ES+ m/z = 279 [M+H]+.

Reference: [1]Current Patent Assignee: ROCHE HOLDING AG - WO2021/219578, 2021, A1 Location in patent: Page/Page column 304-305
[2]Current Patent Assignee: ROCHE HOLDING AG - WO2021/219578, 2021, A1 Location in patent: Page/Page column 304-305
[3]Current Patent Assignee: ROCHE HOLDING AG - WO2021/249896, 2021, A1 Location in patent: Page/Page column 51; 197-198
[4]Current Patent Assignee: ROCHE HOLDING AG - WO2021/249896, 2021, A1 Location in patent: Page/Page column 51; 197-198
[5]Location in patent: experimental part Guillou, Sandrine; Bonhomme, Frédéric J.; Ermolenko, Mikhail S.; Janin, Yves L. [Tetrahedron, 2011, vol. 67, # 44, p. 8451 - 8457]
[6]Current Patent Assignee: CULLGEN SHANGHAI - WO2022/73469, 2022, A1 Location in patent: Paragraph 2262-2264
[7]Current Patent Assignee: CULLGEN SHANGHAI - WO2022/73469, 2022, A1 Location in patent: Paragraph 2262-2264
[8]Current Patent Assignee: THERAVANCE BIOPHARMA, INC. - US2020/188370, 2020, A1 Location in patent: Paragraph 0479; 0672; 0673
[9]Current Patent Assignee: BAYER AG - WO2005/95351, 2005, A1 Location in patent: Page/Page column 73
[10]Current Patent Assignee: SERVIER MONDE - US2015/18328, 2015, A1 Location in patent: Paragraph 1301
[11]Current Patent Assignee: SERVIER MONDE - WO2015/3640, 2015, A1 Location in patent: Page/Page column 284; 285
[12]Axford, Laura; Cohick, Evan; Dales, Natalie; Deng, Lin; Hamann, Lawrence G.; Harrison, Tyler J.; Hollis-Symynkywicz, Micah; Kecman, Sam; Lee, Lac; Loi, Sally; Marcinkeviciene, Jovita; Marro, Martin L.; Papillon, Julien P. N.; Patnaik, Anup; Patterson, Andrew W.; Regard, Jean B.; Ren, Xianglin [Bioorganic and medicinal chemistry, 2020, vol. 28, # 12]
  • 3
  • ethyl 4-fluoro-2-trifluoromethylbenzoate [ No CAS ]
  • [ 866638-72-4 ]
  • [ 1208356-32-4 ]
YieldReaction ConditionsOperation in experiment
90% With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 1h; XI-A-001 Ethyl 4-(4-iodo-3-trifluoromethylpyrazol-1-yl)-2-trifluoromethylbenzoate (XI-A-001) 4-Iodo-3-trifluoromethyl-1H-pyrazole (2.22 g, 8.47 mmol) and potassium carbonate (1.40 g, 10.2 mmol) are added to a solution of ethyl 4-fluoro-2-trifluoromethylbenzoate (2.00 g, 8.47 mmol) in DMF (30 ml), and the mixture is stirred at 60° C. for 1 h. The reaction mixture is diluted with ethyl acetate, washed with water and saturated sodium chloride solution, dried over magnesium sulphate and concentrated under reduced pressure. Purification by chromatography on silica gel gives ethyl 4-(4-iodo-3-trifluoromethylpyrazol-1-yl)-2-trifluoromethylbenzoate (3.65 g, 7.63 mmol, 90%).1H NMR (CDCl3): 1.41 (t, 3H, J=7.1 Hz), 4.43 (q, 2H, J=7.1 Hz), 7.92-7.99 (m, 2H), 8.08 (s, 1H), 8.14-8.14 (m, 1H).
  • 4
  • [ 866638-72-4 ]
  • [ 1341212-31-4 ]
YieldReaction ConditionsOperation in experiment
85% With N-iodo-succinimide In 1,2-dichloro-ethane at 190℃; for 0.75h; Microwave irradiation; 2.18. Iodination of 3f-j, preparation of compounds 4f-j General procedure: The considered 3-trifluoromethylpyrazole (9.6 mmol) and N-iodosuccinimide (2.38 g, 10 mmol) in dichloroethane (14 mL) were heated in a microwave oven as described for each case. The resulting mixture was diluted with ethyl acetate and decolorized with a solution of sodium disulfite. The organic layer was washed with brine five times, dried over magnesium sulfate and concentrated to dryness. The residue was further purified as described below.
  • 6
  • [ 866638-72-4 ]
  • [ 73183-34-3 ]
  • [ 1218790-40-9 ]
YieldReaction ConditionsOperation in experiment
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In N,N-dimethyl-formamide at 90℃; for 2h; 31.2 Step 2: Preparation of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)-1H-pyrazole Step 2: Preparation of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)-1H-pyrazole To a mixture of 4-iodo-3-(trifluoromethyl)-1H-pyrazole (100 mg, 0.38 mmol) and (4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (397 mg, 0.57 mmol) in DMF (3 mL) were added 1,1'-bis-(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (31 mg, 0.04 mmol) and potassium acetate (509 mg, 0.76). The reaction mixture was stirred at 90° C. for 2 hr, then quenched with water and extracted with Et2O. The combined organic layers were washed with brine, dried over anhydrous Na2SO4, and concentrated to afford 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)-1H-pyrazole. LC-MS: m/z 263 (M+H)+.
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In N,N-dimethyl-formamide at 90℃; for 2h; 31.2 Step 2: Preparation of 4-(4,4, 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3 -(trfluoromethyl) -1 Hpyrazole. Step 2: Preparation of 4-(4,4, 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3 -(trfluoromethyl) -1 Hpyrazole. To a mixture of 4-iodo-3-(trifluoromethyl)-1H-pyrazole (100 mg, 0.38 mmol) and (4,4,4’,4’,5,5,5’,5’-octamethyl-2,2’-bi(1,3,2-dioxaborolane) (397 mg, 0.57 mmol) in DIVIF (3 mL) were added 1,1 ‘-bis -(diphenylphosphino)ferrocene-palladium(ll)dichloride dichloromethane complex (31 mg, 0.04 mmol) and potassium acetate (509 mg, 0.76).The reaction mixture was stirred at 90 °C for 2 hr, then quenched with water and extracted with Et20. The combined organic layers were washed with brine, dried over anhydrous Na2SO4, and concentrated to afford 4-(4,4,5 ,5 -tetramethyl- 1,3 ,2-dioxaborolan-2-yl)-3 -(trifluoromethyl)- 1 H-pyrazole.LC-MS: m/z263 (M+H).
  • 7
  • [ 866638-72-4 ]
  • [ 127-00-4 ]
  • 1-[4-iodo-3-(trifluoromethyl)pyrazol-1-yl]propan-2-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4-iodo-3-(trifluoromethyl)-1H-pyrazole With potassium carbonate In tetrahydrofuran at 0 - 20℃; for 0.166667h; Stage #2: 1-Chloro-2-propanol In tetrahydrofuran at 80℃; 1.43 1.43. Intermediate 52: l-[4-iodo-3-(trifluoromethyl)pyrazol-l-yl]propan-2-ol To a solution of 4-iodo-3-trifluoromethyl-lH-pyrazole (1 g, 3.8 mmol, 1.0 equiv) in dry THF (6 mL) at 0°C is added K2C03 (1.6 g, 11.4 mmol, 3.0 equiv). The reaction is stirred at room temperature for 10 min before adding l -chloropropan-2-ol (1.1 g, 11.4 mmol, 3.0 equiv). The reaction is heated at 80°C overnight. The mixture is diluted with EtOAc and washed with brine. The organic layer is dried over sodium sulfate, filtered and concentrated in vacuo. The residue is purified by automated flash chromatography by using Petroleum ether/EtOAc 80/20 to 0/100) to obtain the desired compound. LCMS: MW (calcd): 320; m/z MW (obsd): 321 (M+H).
  • 8
  • [ 866638-72-4 ]
  • [ 21048-16-8 ]
  • 1-(1,4-dioxan-2-ylmethyl)-4-iodo-3-(trifluoromethyl)pyrazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4-iodo-3-(trifluoromethyl)-1H-pyrazole With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 0.166667h; Stage #2: 2-(chloromethyl)-1,4-dioxane In N,N-dimethyl-formamide at 80℃; 1.46 1.46. Intermediate 53: l-(l,4-dioxan-2-ylmethyl)-4-iodo-3-(trifluoromethyl)pyrazole To a solution of 4-iodo-3-trifluoromethyl-lH-pyrazole (350 mg, 1.3 mmol, 1.0 equiv) in dry DMF (2 mL) at 0°C is added K2C03 (359 mg, 2.6 mmol, 2.0 equiv). The reaction is stirred at room temperature for 10 min before adding 2-(chloromethyl)-l,4-dioxane (355 mg, 2.6 mmol, 2.0 equiv). The reaction is heated at 80°C over the weekend. The mixture is diluted with EtOAc and washed with brine. The organic layer is dried over sodium sulfate, filtered and concentrated in vacuo. The residue is purified by automated flash chromatography by using petroleum ether / EtOAc 90/10 to 0/100) to obtain the desired compound. LCMS: MW (calcd): 362; m/z MW (obsd): 363 (M+H).
  • 9
  • [ 866638-72-4 ]
  • [ 627-42-9 ]
  • 4-iodo-1-(2-methoxyethyl)-3-(trifluoromethyl)pyrazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
To a solution of 4-iodo-3-trifluoromethyl-lH-pyrazole (1 g, 3.8 mmol, 1.0 equiv) in dry THF (6 mL) at 0C is added K2CO3 (1.3 g, 9.5 mmol, 2.5 equiv). The reaction is stirred at room temperature for 10 min before adding <strong>[627-42-9]2-chloroethyl methyl ether</strong> (0.87 mL, 9.5 mmol, 2.5 equiv). The reaction is heated at 80C over the weekend. The mixture is diluted with EtOAc and washed with brine. The organic layer is dried over sodium sulfate, filtered and concentrated in vacuo. The residue is purified by automated flash chromatography by using petroleum ether/EtOAc 90/10 to 0/100) to obtain the desired compound. LCMS: MW (calcd): 320; m/z MW (obsd): 321 (M+H).
  • 10
  • [ 866638-72-4 ]
  • [ 156380-34-6 ]
  • 4-iodo-1-tetrahydrofuran-3-yl-3-(trifluoromethyl)pyrazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4-iodo-3-(trifluoromethyl)-1H-pyrazole With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.333333h; Stage #2: methanesulfonic acid tetrahydro-furan-3-yl ester In N,N-dimethyl-formamide at 80℃; for 2h; 1.48 1.48. Intermediate 55: 4-iodo-l-tetrahydrof ran-3-yl-3-(trifl oromethyl)pyrazole To a solution of 4-iodo-3-trifluoromethyl-lH-pyrazole (1 g, 3.8 mmol, 1.0 equiv) in dry DMF (6 mL) at 0°C is added sodium hydride (228 mg, 5.7 mmol, 1.5 equiv). The reaction is stirred at room temperature for 20 min before adding 3-furanol-tetrahydromethanesulfonate (947 mg, 5.7 mmol, 1.5 equiv). The reaction is heated at 80°C for 2h. The mixture is diluted with EtOAc and washed with brine. The organic layer is dried over sodium sulfate, filtered and concentrated in vacuo. The residue is purified by automated flash chromatography by using petroleum ether/EtOAc 90/10 to 0/100) to obtain the desired compound. LCMS: MW (calcd): 332; m/z MW (obsd): 333 (M+H).
  • 11
  • [ 866638-72-4 ]
  • [ 824-94-2 ]
  • C12H10F3IN2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.5 g Stage #1: 4-iodo-3-(trifluoromethyl)-1H-pyrazole With sodium hydride In N,N-dimethyl-formamide at 3 - 20℃; for 1.25h; Stage #2: p-methoxybenzyl chloride In N,N-dimethyl-formamide at 20℃; I.3c Synthesis of 1-(4-methoxybenzyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)-1H-pyrazole To a suspension of NaH (60%, 0.31 g, 1.1 equiv.) in DMF (7.5 mL), a solution of 3g (1.0 g) in DMF (7.5 mL) was added dropwise over about 15 min at about 3 to 7 °C. The reaction mixture was stirred at room temperature for about 1 h and a solution of PMBC1 (1.2 g, 1.05 equiv.) in DMF (4.2 mL) was added dropwise in about 25 min at room temperature. The reaction mixture was stirred at room temperature overnight, poured into water (17 mL), and extracted with diethyl ether (3x17 mL). The ether layers were combined and washed with water (2 x 17 mL) and brine (17 mL), dried over Na2S04, and concentrated in vacuo to give unpurified 3h. Unpurified 3h was absorbed in silica gel (4.3 g) and purified by silica gel chromatography (eluting with 5-25% EtOAc in hexanes) to give 3h (1.5 g).
  • 12
  • [ 866638-72-4 ]
  • (1S,3R)-3-((tert-butoxycarbonyl)amino)cyclopentyl methanesulfonate [ No CAS ]
  • tert-butyl ((1R,3R)-3-(4-iodo-3-(trifluoromethyl)-1H-pyrazol-1-yl)cyclopentyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.32 g With caesium carbonate In N,N-dimethyl-formamide at 100℃; for 16h; Inert atmosphere; tert-butyl((1R,3R)-3-(4-iodo-3-(trifluoromethyl)-1H-pyrazol-1-yl)cyclopentyl)carbamate (17) To a pre-stirred mixture of 4-iodo-3-(trifluoromethyl)-1H-pyrazole (1.20 g, 4.58 mmol) and Cs2CO3 (2.24 g, 6.87 mmol) in DMF (20 mL) under an inert atmosphere was added compound 16 (1.28 g, 4.58 mmol). The mixture was heated at 100 °C overnight. The reaction mixture was cooled to rt and partitioned between EtOAc/water. The organic layer was evaporated and the crude product was purified by silica gel chromatography (5-50% EtOAc/Hep). The desired regioisomer 17 (1.32 g, 65% yield) and the undesired regioisomer (0.239 g, 12%) were isolated. Found ES+ m/z = 389 [M-t-Bu]. The pyrazole regiochemistry was verified through NOE experiments at the final compound stage; major isomer was consistent with desired regioisomer (Structure analysis attached for compound 11).
  • 13
  • [ 866638-72-4 ]
  • [ 51239-46-4 ]
  • C11H9F3IN3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With copper diacetate; triethylamine In dichloromethane at 20℃; 1-(4-(4-chloro-3-iodo-1H-pyrrolo[2,3-b]pyridin-1-yl)phenyl)-N,N-dimethylmethanamine (14) General procedure: To a mixture of compound 13 (0.500 g, 1.80 mmol), (4-(dimethylamino)- methyl)phenyl)boronic acid (0.321 g, 1.80 mmol) and Cu(OAc)2 (0.326 g, 1.80 mmol) in CH2Cl2 (15 mL) was added triethylamine (0.5 mL, 3.59 mmol) and stirred at rt overnight. The mixture was concentrated to about half of the original volume, and the crude residue was purified by silica gel chromatography (1% triethylamine in 10% MeOH/CH2Cl2) to afford compound 14 (0.170 g, 0.413 mmol) in 23% yield. Found ES+ m/z = 412 [M+H]+.
  • 14
  • [ 866638-72-4 ]
  • C9H10BN3O2 [ No CAS ]
  • C13H9F3IN5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With copper diacetate; triethylamine In dichloromethane at 20℃; 1-(4-(4-chloro-3-iodo-1H-pyrrolo[2,3-b]pyridin-1-yl)phenyl)-N,N-dimethylmethanamine (14) General procedure: To a mixture of compound 13 (0.500 g, 1.80 mmol), (4-(dimethylamino)- methyl)phenyl)boronic acid (0.321 g, 1.80 mmol) and Cu(OAc)2 (0.326 g, 1.80 mmol) in CH2Cl2 (15 mL) was added triethylamine (0.5 mL, 3.59 mmol) and stirred at rt overnight. The mixture was concentrated to about half of the original volume, and the crude residue was purified by silica gel chromatography (1% triethylamine in 10% MeOH/CH2Cl2) to afford compound 14 (0.170 g, 0.413 mmol) in 23% yield. Found ES+ m/z = 412 [M+H]+.
  • 15
  • [ 866638-72-4 ]
  • C8H9BF3NO2 [ No CAS ]
  • C12H8F6IN3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With copper diacetate; triethylamine In dichloromethane at 20℃; 1-(4-(4-chloro-3-iodo-1H-pyrrolo[2,3-b]pyridin-1-yl)phenyl)-N,N-dimethylmethanamine (14) General procedure: To a mixture of compound 13 (0.500 g, 1.80 mmol), (4-(dimethylamino)- methyl)phenyl)boronic acid (0.321 g, 1.80 mmol) and Cu(OAc)2 (0.326 g, 1.80 mmol) in CH2Cl2 (15 mL) was added triethylamine (0.5 mL, 3.59 mmol) and stirred at rt overnight. The mixture was concentrated to about half of the original volume, and the crude residue was purified by silica gel chromatography (1% triethylamine in 10% MeOH/CH2Cl2) to afford compound 14 (0.170 g, 0.413 mmol) in 23% yield. Found ES+ m/z = 412 [M+H]+.
  • 16
  • [ 95388-79-7 ]
  • [ 866638-72-4 ]
  • tert-butyl (4-(4-iodo-3-(trifluoromethyl)-1H-pyrazol-1-yl)butyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 16h; tert-butyl (4-(4-iodo-3-(trifluoromethyl)-1H-pyrazol-1-yl)butyl)carbamate (20) To a mixture of 4-iodo-3-trifluoromethyl-1H-pyrazole (0.350 g, 1.34 mmol) and K2CO3 (0.277 g, 2.00 mmol) in DMF (3.0 mL) was added t-butyl-4-chlorobutylcarbamate (0.305 mg, 1.47 mmol), and the mixture was stirred at 50 °C for 16 h. After allowing to cool to rt, the mixture was directly loaded onto a silica column and purified via silica gel chromatography (5-50% EtOAc/Hep) to give 20 (0.497 g, 1.15 mmol) in 86% yield. Found ES+ m/z = 378 [M-t-Bu]+.
  • 17
  • [ 866638-72-4 ]
  • [ 120158-04-5 ]
  • C12H15F3IN3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 16h; tert-butyl (4-(4-iodo-3-(trifluoromethyl)-1H-pyrazol-1-yl)butyl)carbamate (20) General procedure: To a mixture of 4-iodo-3-trifluoromethyl-1H-pyrazole (0.350 g, 1.34 mmol) and K2CO3 (0.277 g, 2.00 mmol) in DMF (3.0 mL) was added t-butyl-4-chlorobutylcarbamate (0.305 mg, 1.47 mmol), and the mixture was stirred at 50 °C for 16 h. After allowing to cool to rt, the mixture was directly loaded onto a silica column and purified via silica gel chromatography (5-50% EtOAc/Hep) to give 20 (0.497 g, 1.15 mmol) in 86% yield. Found ES+ m/z = 378 [M-t-Bu]+.
  • 18
  • [ 866638-72-4 ]
  • [ 120158-03-4 ]
  • C11H13F3IN3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 16h; tert-butyl (4-(4-iodo-3-(trifluoromethyl)-1H-pyrazol-1-yl)butyl)carbamate (20) General procedure: To a mixture of 4-iodo-3-trifluoromethyl-1H-pyrazole (0.350 g, 1.34 mmol) and K2CO3 (0.277 g, 2.00 mmol) in DMF (3.0 mL) was added t-butyl-4-chlorobutylcarbamate (0.305 mg, 1.47 mmol), and the mixture was stirred at 50 °C for 16 h. After allowing to cool to rt, the mixture was directly loaded onto a silica column and purified via silica gel chromatography (5-50% EtOAc/Hep) to give 20 (0.497 g, 1.15 mmol) in 86% yield. Found ES+ m/z = 378 [M-t-Bu]+.
  • 19
  • [ 866638-72-4 ]
  • C11H21NO5S [ No CAS ]
  • C14H19F3IN3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate In N,N-dimethyl-formamide at 100℃; for 16h; Inert atmosphere; tert-butyl((1R,3R)-3-(4-iodo-3-(trifluoromethyl)-1H-pyrazol-1-yl)cyclopentyl)carbamate (17) General procedure: To a pre-stirred mixture of 4-iodo-3-(trifluoromethyl)-1H-pyrazole (1.20 g, 4.58 mmol) and Cs2CO3 (2.24 g, 6.87 mmol) in DMF (20 mL) under an inert atmosphere was added compound 16 (1.28 g, 4.58 mmol). The mixture was heated at 100 °C overnight. The reaction mixture was cooled to rt and partitioned between EtOAc/water. The organic layer was evaporated and the crude product was purified by silica gel chromatography (5-50% EtOAc/Hep). The desired regioisomer 17 (1.32 g, 65% yield) and the undesired regioisomer (0.239 g, 12%) were isolated. Found ES+ m/z = 389 [M-t-Bu]. The pyrazole regiochemistry was verified through NOE experiments at the final compound stage; major isomer was consistent with desired regioisomer (Structure analysis attached for compound 11).
  • 20
  • [ 110-87-2 ]
  • [ 866638-72-4 ]
  • 4-iodo-1-(tetrahydro-2H-pyran-2-yl)-3-(trifluoromethyl)-1H-pyrazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
33 g With toluene-4-sulfonic acid In tetrahydrofuran at 80℃; for 2h; Inert atmosphere; 78 Example 78: Synthesis of 4-iodo-1-(tetrahydro-2H-pyran-2-yl)-3-(trifluoromethyl)-1H-pyrazole To a solution of 101 (25.0 g, 95.4 mmol) in THF (300 mL) was added TosOH (1.6 g, 9.5 mmol) and dihydropyran (40.1 g, 477.0 mmol). The mixture was stirred for 2 h at 80° C. The reaction was diluted with sat. sodium bicarbonate aq. (300 mL) and extracted with EA (300 mL*3). The combined organic layers were dried (Na2SO4) and concentrated in vacuum. The residue was purified by column (0-5% of EA in PE) to afford crude 102 (33.0 g) as light yellow oil.
  • 21
  • [ 866638-72-4 ]
  • [ 76-83-5 ]
  • 4-iodo-3-(trifluoromethyl)-1-trityl-1H-pyrazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
66.46% Stage #1: 4-iodo-3-(trifluoromethyl)-1H-pyrazole With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Stage #2: [chloro(diphenyl)methyl]benzene In tetrahydrofuran; mineral oil at 10℃; for 16h; 171.3 Step 3: 4-iodo-3-(trifluoromethyl)-l-trityl-lH-pyrazole To a solution of 4-iodo-3-(trifluoromethyl)-lH-pyrazole (222.0 g, 847.43 mmol, 1 eq) in THF (2220 mL) was added 60% sodium hydride (37.28 g, 932.17 mmol, 1.1 eq) at 0 °C, the mixture was stirred 0 °C for 0.5 h, then triphenylmethyl chloride (259.87 g, 932.17 mmol, 1.1 eq) was added. The mixture was warmed to 10 °C and stirred for 16 h. The mixture was quenched with sat. NH4CI (500 mL) and extracted with EtOAc (300 mL x 2), washed with brine (700 mL), dried over sodium sulfate, filtered and concentrated in vacuum to give crude product, wH-ich was purified by silica gel column chromatography (eluting petroluem ehter/EtOAc = 100/1) to give 4-iodo-3-(trifluoromethyl)-l-trityl-pyrazole (284 g, 563.17 mmol,66.46% yield) as wH-ite solid. NMR (400 MHz, CHLOROFORM-d) d = 7.42 (s, 1H), 7.34-7.37 (m, 9H), 7.09 - 7.12 (m, (1496) 6H) ppm.
45.34% Stage #1: 4-iodo-3-(trifluoromethyl)-1H-pyrazole With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: [chloro(diphenyl)methyl]benzene In tetrahydrofuran at 10℃; for 16h; Inert atmosphere; 8.2 4-Iodo-3-(trifluoromethyl)-1-trityl-pyrazole To a solution of 4-iodo-3-(trifluoromethyl)-1H-pyrazole (110.0 g, 419.9 mmol, 1 eq) in THF (1100 mL) was added sodium hydride, 60% in oil (18.47 g, 461.88 mmol, 1.1 eq) at 0°C, the mixture was stirred for 0.5h at 0°C, then triphenylmethyl chloride (128.76 g, 461.88 mmol, 1.1 eq) was added to the solution. The mixture was stirred for 16 h at 10 °C. The mixture was quenched with sat. NH4Cl (500 mL) and extracted with EtOAc (300 mL x 2), washed with brine (700 mL), dried over sodium sulfate, filtered and concentrated in vacuum to give crude product, which was purified by silica gel column chromatography eluting Petroluem ehter/EtOAc=100/1 to give the title compound (96 g, 190.37 mmol, 45.34% yield) as white solid. MS (ESI, m/z): 543.0 [M+K]+
45.34% Stage #1: 4-iodo-3-(trifluoromethyl)-1H-pyrazole With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: [chloro(diphenyl)methyl]benzene In tetrahydrofuran at 10℃; for 16h; Inert atmosphere; 8.2 4-Iodo-3-(trifluoromethyl)-1-trityl-pyrazole To a solution of 4-iodo-3-(trifluoromethyl)-1H-pyrazole (110.0 g, 419.9 mmol, 1 eq) in THF (1100 mL) was added sodium hydride, 60% in oil (18.47 g, 461.88 mmol, 1.1 eq) at 0°C, the mixture was stirred for 0.5h at 0°C, then triphenylmethyl chloride (128.76 g, 461.88 mmol, 1.1 eq) was added to the solution. The mixture was stirred for 16 h at 10 °C. The mixture was quenched with sat. NH4Cl (500 mL) and extracted with EtOAc (300 mL x 2), washed with brine (700 mL), dried over sodium sulfate, filtered and concentrated in vacuum to give crude product, which was purified by silica gel column chromatography eluting Petroluem ehter/EtOAc=100/1 to give the title compound (96 g, 190.37 mmol, 45.34% yield) as white solid. MS (ESI, m/z): 543.0 [M+K]+
  • 22
  • [ 866638-72-4 ]
  • [ 590-17-0 ]
  • 2-[4-iodo-3-(trifluoromethyl)pyrazol-1-yl]acetonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
87.03% With potassium carbonate In propan-2-one at -60 - 0℃; for 4h; Inert atmosphere; 64.4 2-[4-Iodo-3-(trifluoromethyl)pyrazol-1-yl]acetonitrile To a mixture of 4-iodo-3-(trifluoromethyl)-1H-pyrazole (10 g, 38.17 mmol, 1 eq) in acetone (200 mL) was added potassium carbonate (6.33 g, 45.81 mmol, 1.2 eq) and 2-bromoacetonitrile (6.87 g, 57.26 mmol, 1.5 eq) at -60 C . The mixture was stirred at 0 C for 4 h. The mixture was poured into water (50 mL). The aqueous phase was extracted with EtOAc (50 mL x 2). The combined organic phase was washed with brine (100 mL), dried over anhydrous Na2SO4 and concentrated in vacuum. The residue was purified by silical gel column chromatography (petroleum ether/EtOAc=20/1) to afford the title compound (10 g, 33.2 mmol, 87.03% yield) as a colorless oil.1H NMR (400 MHz, CHLOROFORM-d) Shift 7.74 (d, J=0.73 Hz, 1H), 5.14 (s, 2H).
87.03% With potassium carbonate In propan-2-one at -60 - 0℃; for 4h; Inert atmosphere; 64.4 2-[4-Iodo-3-(trifluoromethyl)pyrazol-1-yl]acetonitrile To a mixture of 4-iodo-3-(trifluoromethyl)-1H-pyrazole (10 g, 38.17 mmol, 1 eq) in acetone (200 mL) was added potassium carbonate (6.33 g, 45.81 mmol, 1.2 eq) and 2-bromoacetonitrile (6.87 g, 57.26 mmol, 1.5 eq) at -60 C . The mixture was stirred at 0 C for 4 h. The mixture was poured into water (50 mL). The aqueous phase was extracted with EtOAc (50 mL x 2). The combined organic phase was washed with brine (100 mL), dried over anhydrous Na2SO4 and concentrated in vacuum. The residue was purified by silical gel column chromatography (petroleum ether/EtOAc=20/1) to afford the title compound (10 g, 33.2 mmol, 87.03% yield) as a colorless oil.1H NMR (400 MHz, CHLOROFORM-d) Shift 7.74 (d, J=0.73 Hz, 1H), 5.14 (s, 2H).
With potassium carbonate In propan-2-one at -60 - 20℃; for 4h; 499.4 Step 4: 2-[4-iodo-3-(trifluoromethyl)pyrazol-1-yl]acetonitrile To a mixture of 4-iodo-3-(trifluoromethyl)-1H-pyrazole (30 g, 114.52 mmol) in acetone (600 mL) was added potassium carbonate (18.99 g, 137.42 mmol) and 2-bromoacetonitrile (16.48 g, 137.42 mmol) at -60 C. The mixture was stirred at 20 C for 4 h. The mixture was poured into water (200 mL). The aqueous phase was extracted with EtOAc (200 mL x 2). The combined organic phase was washed with brine (300 mL), dried over anhydrous Na2SO4 and concentrated in vacuum. The residue was purified by silica gel column chromatography (petroleum ether/EtOAc=20/1) to yield the title compound as a colorless oil (30 g, 99.66 mmol, 87.03% yield). MS(m/e): 334.9 (M+H).
With potassium carbonate In propan-2-one at -60 - 20℃; for 4h; 499.4 Step 4: 2-[4-iodo-3-(trifluoromethyl)pyrazol-1-yl]acetonitrile To a mixture of 4-iodo-3-(trifluoromethyl)-1H-pyrazole (30 g, 114.52 mmol) in acetone (600 mL) was added potassium carbonate (18.99 g, 137.42 mmol) and 2-bromoacetonitrile (16.48 g, 137.42 mmol) at -60 C. The mixture was stirred at 20 C for 4 h. The mixture was poured into water (200 mL). The aqueous phase was extracted with EtOAc (200 mL x 2). The combined organic phase was washed with brine (300 mL), dried over anhydrous Na2SO4 and concentrated in vacuum. The residue was purified by silica gel column chromatography (petroleum ether/EtOAc=20/1) to yield the title compound as a colorless oil (30 g, 99.66 mmol, 87.03% yield). MS(m/e): 334.9 (M+H).

  • 23
  • [ 866638-72-4 ]
  • [ 142356-34-1 ]
  • tert-butyl (6-(4-iodo-3-(trifluoromethyl)-1H-pyrazol-1-yl)hexyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% With Cs2CO3; sodium iodide In N,N-dimethyl-formamide at 100℃; for 1h; 508.2 Step 2. Synthesis of tert-butyl (6- (4-iodo-3- (trifluoromethyl) -1H-pyrazol-1-yl) hexyl) carbamate To a mixture of 4-iodo-3- (trifluoromethyl) -1H-pyrazole (500 mg, 1.9 mmol) and tert-butyl N- (7-bromoheptyl) carbamate (618 mg, 2.1 mmol) in DMF (10 mL) were added NaI (429 mg, 2.8 mmol) and Cs 2CO 3 (1.24 g, 3.8 mmol). After the reaction was stirred at 100 °C for 1 h, it was quenched with water, and extracted with EtOAc. The organic phase was washed with water, dried over Na 2SO 4, filtered, and concentrated. The resulting residue was purified by reverse phase chromatography (0-70%MeCN in H 2O) to provide the title compound (500 mg, yield: 57%) as bright oil. MS (ESI) m/z = 462.1 [M+H] +.
57% With Cs2CO3; sodium iodide In N,N-dimethyl-formamide at 100℃; for 1h; 508.2 Step 2. Synthesis of tert-butyl (6- (4-iodo-3- (trifluoromethyl) -1H-pyrazol-1-yl) hexyl) carbamate To a mixture of 4-iodo-3- (trifluoromethyl) -1H-pyrazole (500 mg, 1.9 mmol) and tert-butyl N- (7-bromoheptyl) carbamate (618 mg, 2.1 mmol) in DMF (10 mL) were added NaI (429 mg, 2.8 mmol) and Cs 2CO 3 (1.24 g, 3.8 mmol). After the reaction was stirred at 100 °C for 1 h, it was quenched with water, and extracted with EtOAc. The organic phase was washed with water, dried over Na 2SO 4, filtered, and concentrated. The resulting residue was purified by reverse phase chromatography (0-70%MeCN in H 2O) to provide the title compound (500 mg, yield: 57%) as bright oil. MS (ESI) m/z = 462.1 [M+H] +.
  • 24
  • [ 866638-72-4 ]
  • [ 1215358-53-4 ]
  • 2-cyclopropyl-3-(1H-pyrazol-4-yl)quinoxaline [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In ethanol; lithium hydroxide monohydrate; toluene Inert atmosphere; Reflux; 479.2 Step 2. Synthesis of 2-cyclopropyl-3- (1H-pyrazol-4-yl) quinoxaline A mixture of 2-chloro-3-cyclopropyl-quinoxaline (300 mg, 1.47 mmol), 4- (4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) -1H-pyrazole (284.44 mg, 1.47 mmol), K 2CO 3 (203 mg, 1.47 mmol) and Pd (PPh 4) 3 (50 mg, 1.47 mmol) in toluene (10 mL), ethanol (5 mL) and water (2.5 mL) was heated at reflux overnight under N 2. The mixture was cooled to rt, and concentrated. The resulting residue was purified by reverse phase chromatography to provide the title compound (200 mg, yield: 57%) as light-yellow solid. MS (ESI) m/z = 237.2 [M+H] +.
57% With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In ethanol; lithium hydroxide monohydrate; toluene Inert atmosphere; Reflux; 479.2 Step 2. Synthesis of 2-cyclopropyl-3- (1H-pyrazol-4-yl) quinoxaline A mixture of 2-chloro-3-cyclopropyl-quinoxaline (300 mg, 1.47 mmol), 4- (4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) -1H-pyrazole (284.44 mg, 1.47 mmol), K 2CO 3 (203 mg, 1.47 mmol) and Pd (PPh 4) 3 (50 mg, 1.47 mmol) in toluene (10 mL), ethanol (5 mL) and water (2.5 mL) was heated at reflux overnight under N 2. The mixture was cooled to rt, and concentrated. The resulting residue was purified by reverse phase chromatography to provide the title compound (200 mg, yield: 57%) as light-yellow solid. MS (ESI) m/z = 237.2 [M+H] +.
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