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[ CAS No. 925180-06-9 ]

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Chemical Structure| 925180-06-9
Chemical Structure| 925180-06-9
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CAS No. :925180-06-9 MDL No. :MFCD06804869
Formula : C6H9BrN2O Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :205.05 g/mol Pubchem ID :-
Synonyms :

Safety of [ 925180-06-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 925180-06-9 ]

  • Downstream synthetic route of [ 925180-06-9 ]

[ 925180-06-9 ] Synthesis Path-Downstream   1~9

  • 1
  • [ 2075-45-8 ]
  • [ 627-18-9 ]
  • [ 925180-06-9 ]
YieldReaction ConditionsOperation in experiment
46% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12h; 3 The synthesis of 3-(4-bromo-lH-pyrazol-l-yl)propan-l-ol (0019-2). To a stirred solution of 0019-1 (2.7 g, 18.2 mmol) in DMF (50 ml) was added 3- bromopropan-l-ol (2.8 g, 20.0 mmol) and K2CO3 (3.8 g, 27.3 mmol). The resulting reaction mixture was stirred for 12 h at rt. Then added water, the aqueous phase was extracted with di chi orom ethane, the combined organic phases were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo , purified by C.C. to give the desired product 0019-2 (1.7 g, yield: 46%) as colorless oil.
With caesium carbonate In N,N-dimethyl-formamide at 50℃; 7.A Cesium carbonate (1.11 g, 3.40 mmol) and 4-bromo-lH-pyrazole (250 mg, 1.70 mmol) were suspended in DMF (8.5 mL). 3-Bromopropan-l-ol (178 μL, 2.041 mmol) was added and the mixture heated to 500C overnight. The mixture was cooled to room temperature, filtered, and the solvent from the filtrate was evaporated under vacuum to give a residue. The residue was purified by column chromatography (gradient: 0 to 2.5% methanol in dichloromethane) to give the title compound. MS [M+H] found 205. 1H NMR (400 MHz, CHLOROFORM-J) δ ppm 2.06 (quin, 2 H), 2.33 (quin, J=6.32 Hz, 1 H), 3.65 (br. s., 1 H), 4.21 - 4.32 (m, 2 H), 4.34 (t, J=6.06 Hz, 1 H), 4.88 (br. s., 1 H), 7.41 - 7.52 (m, 2 H).
With caesium carbonate In N,N-dimethyl-formamide at 50℃; 98.A Cesium carbonate (1.11 g, 3.40 mmol) and 4-bromo-l/f-pyrazole (250 mg, 1.70 mmol) were suspended in DMF (8.5 rnL). 3-Bromopropan-l-ol (178 μL, 2.041 mmol) was added and heated to 500C overnight. The mixture was cooled to room temperature, filtered, and solvent from the filtrate was evaporated under vacuum to give a residue. The residue was purified by column chromatography (gradient: 0 to 2.5% methanol in dichloromethane) to give the title compound. MS [M+H] found 205. 1H NMR (400 MHz, CHLOROFORM- d) δ ppm 2.06 (quin, 2 H), 2.33 (quin, J=6.32 Hz, 1 H), 3.65 (br. s., 1 H), 4.21 - 4.32 (m, 2 H), 4.34 (t, J=6.06 Hz, 1 H), 4.88 (br. s., 1 H), 7.41 - 7.52 (m, 2 H)
  • 2
  • [ 925180-06-9 ]
  • [ 73183-34-3 ]
  • [ 1000802-50-5 ]
YieldReaction ConditionsOperation in experiment
100% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 120℃; for 2h; Microwave irradiation; 121 Preparation of intermediate 145: 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H- pyrazol-1-yl]propan-1-ol To a solution of 4-bromo-1-(3-hydroxypropyl)-1H-pyrazole (0.410 g, 2.0 mmol) in dioxane (4 mL) was added at RT bis(pinacolato)diboron (0.609 g, 2.4 mmol), KOAc (0.589 g, 6.0 mmol) and PdCl2(dppf).DCM (0.082 g, 0.1 mmol). The resulting reaction mixture was stirred under microwave irradiation at 100°C for 2 h. The residue was diluted with water and extracted with ethyl acetate twice. The combined organic layer was dried over anhydrous sodium sulfate affording 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]propan-1-ol 145 as a brown oil, which was used in the next step without further purification. Yield: 0.504 g of intermediate 145 (quantitative) LCMS method F: [M+H]+ = 253.2, tR = 1.91 min
100% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 120℃; for 2h; Microwave irradiation; 121 Preparation of intermediate 145: 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H- pyrazol-1-yl]propan-1-ol To a solution of 4-bromo-1-(3-hydroxypropyl)-1H-pyrazole (0.410 g, 2.0 mmol) in dioxane (4 mL) was added at RT bis(pinacolato)diboron (0.609 g, 2.4 mmol), KOAc (0.589 g, 6.0 mmol) and PdCl2(dppf).DCM (0.082 g, 0.1 mmol). The resulting reaction mixture was stirred under microwave irradiation at 100°C for 2 h. The residue was diluted with water and extracted with ethyl acetate twice. The combined organic layer was dried over anhydrous sodium sulfate affording 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]propan-1-ol 145 as a brown oil, which was used in the next step without further purification. Yield: 0.504 g of intermediate 145 (quantitative) LCMS method F: [M+H]+ = 253.2, tR = 1.91 min
With sodium acetate In N,N-dimethyl-formamide at 80℃; Inert atmosphere; 7.B; 98.B PdCl2(dppf) (28.7 mg, 0.039 mmol), sodium acetate (193 mg, 2.355 mmol), 3-(4- bromo-l/f-pyrazol-l-yl)propan-l-ol (161 mg, 0.785 mmol) and 4,4,4',4',5,5,5',5'- octamethyl-2,2'-bi(l,3,2-dioxaborolane) (598 mg, 2.355 mmol) were added to an oven- dried Schlenk flask. The solids were subjected to 4 cycles of nitrogen and vacuum. DMF (10.5mL) was added and the mixture was heated to 800C overnight. The reaction mixture was cooled to room temperature, filtered, and the filtrate was purified by mass-triggered HPLC (gradient: 25 to 30% ACN in water containing 0.05% TFA) to give the title compound. MS [M+H] found 253
  • 3
  • [ 925180-06-9 ]
  • [ 1254836-92-4 ]
  • [ 1254837-92-7 ]
YieldReaction ConditionsOperation in experiment
With sodium hydrogencarbonate In 1,4-dioxane at 115℃; for 0.25h; microwave tube; 98.C PdCl2(dppf) (4.60 mg, 6.28 μmol), N-(4-bromo-2-(trifluoromethoxy)benzyl)-2,6- dioxo-1 -(pyridin-2-ylmethyl)- 1,2, 3, 6-tetrahydropyrimidine-4-carboxamide (62.7 mg, 0.126 mmol), 3-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyrazol-l-yl)propan- l-ol (38 mg, 0.151 mmol) were suspended in dioxane (628 μL) and sodium bicarbonate (sat., 628 μL) in a microwave tube. The tube was capped and was heated in the microwave to 115°C for 15 minutes. Solvent was evaporated under vacuum to give a residue, which was sonicated with methanol (2 mL) and filtered. The filtrate was purified by mass- triggered HPLC (gradient: 20 to 25% ACN in water containing 0.05% TFA) to give the title compound. MS [M+H] found 545.
  • 4
  • [ 925180-06-9 ]
  • [ 1257996-05-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 0.75 h / 100 °C / Microwave irradiation 2.1: hydrogen / palladium 10% on activated carbon / ethanol; water / 2 h / 20 °C 3.1: trifluoroacetic acid / 2,2,2-trifluoroethanol / 1 h / 105 °C / Microwave irradiation 3.2: 2 h / 0 - 20 °C
  • 5
  • [ 925180-06-9 ]
  • [ 1380302-86-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 0.75 h / 100 °C / Microwave irradiation 2.1: hydrogen / palladium 10% on activated carbon / ethanol; water / 2 h / 20 °C 3.1: trifluoroacetic acid / 2,2,2-trifluoroethanol / 1 h / 105 °C / Microwave irradiation 3.2: 2 h / 0 - 20 °C 4.1: sodium iodide / butanone / 7 h / 120 °C / Microwave irradiation
  • 6
  • [ 925180-06-9 ]
  • [ 1257998-32-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 0.75 h / 100 °C / Microwave irradiation 2: hydrogen / palladium 10% on activated carbon / ethanol; water / 2 h / 20 °C
  • 7
  • [ 925180-06-9 ]
  • [ 1380302-85-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: potassium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 0.75 h / 100 °C / Microwave irradiation 2.1: hydrogen / palladium 10% on activated carbon / ethanol; water / 2 h / 20 °C 3.1: trifluoroacetic acid / 2,2,2-trifluoroethanol / 1 h / 105 °C / Microwave irradiation 3.2: 2 h / 0 - 20 °C 4.1: sodium iodide / butanone / 7 h / 120 °C / Microwave irradiation 5.1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / N,N-dimethyl-formamide; 1,2-dichloro-ethane / 72 h
  • 8
  • [ 925180-06-9 ]
  • [ 1257996-65-8 ]
  • [ 1257998-33-6 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In 1,4-dioxane; water at 100℃; for 0.75h; Microwave irradiation; 1 Compound 1 D: 4-[1 -(3-Hydroxypropyl)-1 H-pyrazol-4-yl]-2-methyl-7-nitro-2,3-dihydro-1 H- isoindol-1 -oneA suspension of 2-methyl-7-nitro-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-2,3- dihydro-1 /-/-isoindol-1-one (Compound 11, 1.825 g, 5.736 mmol), 3-(4-bromo-1 /-/-pyrazol-1 - yl)propan-1 -ol (1 .45 g, 7.07 mmol), [1 ,1 - bis(diphenylphosphino)ferrocene]dichloropalladium(ll), complex with dichloromethane (1 :1 ) (510 mg, 0.62 mmol), and potassium carbonate (2.4 g, 17.3 mmol) in dioxane (20 mL) and H20 (5 mL) was irradiated in a microwave reactor for 45 min at 100 °C. The reaction mixture was poured into water and extracted with CH2CI2 three times. The combined organic layers were washed with brine, dried over anhydrous Na2S04, filtered, concentrated in vacuo, and purified using a Teledyne ISCO CombiFlash Rf system (eluting with 0-15% MeOH:CH2CI2) to isolate the desired compound as 920 mg as a yellow solid. 1H NMR (400 MHz, DMSO-c/6) δ 8.35 (s, 1 H), 8.05 (s, 1 H), 7.99 (d, J = 8.3 Hz, 1 H), 7.88 (d, J = 8.3 Hz, 1 H), 4.72 (s, 2H), 4.63 (t, J = 5.1 Hz, 1 H), 4.25 (t, J = 7.1 Hz, 2H), 3.43 (q, J = 6.1 Hz, 2H), 3.1 1 (s, 3H), 1 .98 (quin, J = 6.6 Hz, 2H). HRMS (ESI): m/z 317.1 1 [M+H]+. UPLC: iR = 0.91 min (UPLC-TOF: polar_3min).
  • 9
  • [ 480424-93-9 ]
  • [ 925180-06-9 ]
  • N-(3-(1-(3-hydroxypropyl)-1H-pyrazol-4-yl)phenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
16% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 100℃; for 5h; 3 The synthesis of N-(3-(l-(3-hydroxypropyl)-lH-pyrazol-4-yl)phenyl)acetamide To a stirred solution of compound 0019-2 (240 mg, 1.2 mmol) in dioxane/water (10 mL/2 mL) was added 0015-5 (305 mg, 1.2 mmol), K2CO3 (484 mg, 3.5 mmol), Pd(dppf)Cl2 (80 mg). The resulting reaction mixture was heated to 100 °C and stirred for 5 h and concentrated in vacuo to remove the solvent, then added water, the aqueous phase was extracted with dichloromethane, the combined organic phases were dried over anhydrous sodium sulfate, filtered, and concentrated, the crude was purified by prep-HPLC to give the desired product SU20666-0019 (49 mg, yield: 16%) as a white solid.[0761] LC-MS (Agilent LCMS 1200-6120, Column: Waters X-Bridge C18 (50 mm*4.6 mm*3.5 pm); Column Temperature: 40 °C; Flow Rate: 2.0 mL/min; Mobile Phase: from95% [water + 10 mM NH4HCO3] and 5% [CH3CN] to 0% [water + 10 mM NH4HCO3] and 100% [CH3CN] in 1.6 min, then under this condition for 1.4 min, finally changed to 95% [water + 10 mM NH4HCO3] and 5% [CH3CN] in 0.1 min and under this condition for 0.7 min), Purity: 95.43%, Rt = 1.389 min; MS Calcd. : 259.1; MS Found: 260.2 [M+H]+. [0762] HPLC (Agilent HPLC 1200, Column: Waters X-Bridge C18 (150 mm*4.6 mm*3.5 pm); Column Temperature: 40 °C; Flow Rate: 1.0 mL/min; Mobile Phase: from 95% [water + 10 mM NH4HCO3] and 5% [CH3CN] to 0% [water + 10 mM NH4HCO3] and 100%[CH3CN] in 10 min, then under this condition for 5 min, finally changed to 95% [water + 10 mM NH4HCO3] and 5% [CH3CN] in 0.1 min and under this condition for 5 min), Purity: 99.82%, Rt = 6.418 min.[0763] NMR (400 MHz, DMSO-i) d 1.92-1.97 (2H, m), 2.05 (3H, s), 3.40-3.42 (2H, m), 4.18 (2H, t, J= 6.8 Hz), 4.62 (1H, t, J = 5.2 Hz), 7.21-7.28 (2H, m), 7.38 (1H, d, J = 7.2 Hz), 7.74-7.76 (2H, m), 8.07 (1H, s), 9.93 (1H, s).
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