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Chemical Structure| 1414570-28-7 Chemical Structure| 1414570-28-7

Structure of 1414570-28-7

Chemical Structure| 1414570-28-7

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Product Details of [ 1414570-28-7 ]

CAS No. :1414570-28-7
Formula : C10H10BrN3
M.W : 252.11
SMILES Code : NC1=C(C)C(Br)=NN1C2=CC=CC=C2
MDL No. :MFCD30287358

Safety of [ 1414570-28-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H312-H332
Precautionary Statements:P280

Application In Synthesis of [ 1414570-28-7 ]

* 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 [ 1414570-28-7 ]

[ 1414570-28-7 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 1002309-52-5 ]
  • [ 1414570-28-7 ]
  • [ 1414581-58-0 ]
YieldReaction ConditionsOperation in experiment
59% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; at 95℃; for 16h;Sealed tube; Preparation G 5-(5-amino-4-methyl- 1 -phenyl- 1 H-pyrazol-3-yl)- 1 -methylpyridin-2( 1 H)-one1005491 3 -bromo-4-methyl- 1 -phenyl- 1 H-pyrazol-5-amine [Preparation F] (763 mg,3.03 mmol), 1 -methyl-5-(4,4,5,5-tetramethyl- 1,3 ,2-dioxaborolan-2-yl)pyridin-2( 1 H)one (1.42 g, 6.05 mmol), K2C03 (1.67 g, 12.1 nimol) and Pd(PPh3)4 (350 mg, 0.30 mmol) were combined in toluene (10 mL), water (5 mL) and EtOH (2.5 mL) and warmed to 95 °C in a sealed tube for 16 hours. The cooled mixture was filtered and the filtrate partitioned between water (30 mL) and EtOAc (30 mL). The aqueous layer was extracted with EtOAc (2 x 20 mE) and the combined organic phases were washed with brine (20 mL), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica column chromatography eluting with 2percent MeOHJDCM to afford the title compound (504 mg, 59percent yield) as a yellow foam. MS (apci) m/z = 281.2 (M+H).
59% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; at 95℃; for 16h;Sealed tube; Intermediate 5 5-(5-amino-4-methyl- 1 -phenyl- 1 H-pyrazol-3-yl)- 1 -methylpyridin-2( 1 H)-one1003011 3-Bromo-4-methyl-1-phenyl-1H-pyrazol-5-amine [Intermediate 4] (763 mg,3.03 mmol), 1 -methyl-5-(4,4,5,5-tetramethyl- 1,3 ,2-dioxaborolan-2-yl)pyridin-2( 1 H)one (1.42 g, 6.05 mmol), K2C03 (1.67 g, 12.1 mmol) and Pd(PPh3)4 (350 mg, 0.30 mmol) were combined in toluene (10 mL), water (5 mL) and EtOH (2.5 mE) and warmed to 95 °C in a sealed tube for 16 hours. The cooled mixture was filtered and the filtrate partitioned between water (30 mL) and EtOAc (30 mL). The aqueous layer was extracted with EtOAc (2 x 20 mE) and the combined organic phases were washed with brine (20 mL), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica column chromatography eluting with 2percent MeOH/DCM to afford the title compound (504 mg, 59percent yield) as a yellow foam. MS (apci) mz = 281.2 (M+I{).
59% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; at 95℃; for 16h;Sealed tube; Intermediate 5 5-(5-amino-4-methyl- 1 -phenyl- 1 H-pyrazol-3 -vD- 1 -methylpyridin-2( 1 HVone [00359] 3-Bromo-4-methyl-l -phenyl- lH-pyrazol-5-amine [Intermediate 4] (763 mg, 3.03 mmol), l-methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyridin-2(lH)one (1.42 g, 6.05 mmol), K2C03 (1.67 g, 12.1 mmol) and Pd(PPh3)4 (350 mg, 0.30 mmol) were combined in toluene (10 mL), water (5 mL) and EtOH (2.5 mL) and warmed to 95 °C in a sealed tube for 16 hours. The cooled mixture was filtered and the filtrate partitioned between water (30 mL) and EtOAc (30 mL). The aqueous layer was extracted with EtOAc (2 x 20 mL) and the combined organic phases were washed with brine (20 mL), dried over Na2S04, filtered and concentrated in vacuo. The residue was purified by silica column chromatography eluting with 2percent MeOH/DCM to afford the title compound (504 mg, 59percent yield) as a yellow foam. MS (apci) m/z = 281.2 (M+H).
59% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; at 95℃; for 16h;Sealed tube; 1004931 Step C: Preparation of 5-(5-amino-4-methyl-1-phenyl-1H-pyrazol-3-yl)-1- methylpyridin-2( 111)-one: 3-bromo-4-methyl- 1 -phenyl- 1 H-pyrazol-5-amine (763 mg, 3.03 mmol), 1 -methyl-5-(4,4,5,5-tetramethyl- 1,3 ,2-dioxaborolan-2-yl)pyridin-2( 1 H)one (1.42 g, 6.05 mmol), K2C03 (1.67 g, 12.1 mmol) and Pd(PPh3)4 (350 mg, 0.30 mmol) were combined in toluene (10 mE), water (5 mL) and EtOH (2.5 mL). The reaction mixture was heated to 95°C in a sealed tube for 16 hours. The mixture was cooled, filtered and the filtrate was concentrated. The residue was partitioned between water (30 mL) and EtOAc (30 mL). The organic layer was removed and the aqueous layer was extracted with EtOAc (2 x 20 mL). The combined organic phases were washed with saturated NaC1 (20 mL), dried over Na2SO4, filtered and concentrated. The residue was purified by silica column chromatography eluting with 2percent MeOHJDCM to afford the title compound (504 mg, 59percent yield) as a yellow foam. MS (apci) mlz = 281.2 (M+H).
59% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; at 95℃; for 16h;Sealed tube; 3-Bromo-4-methyl-l -phenyl- lH-pyrazol-5 -amine (763 mg, 3.03 mmol), l-methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyridin-2(lH)one (1.42 g, 6.05 mmol), K2C03 (1.67 g, 12.1 mmol) and Pd(PPh3)4 (350 mg, 0.30 mmol) were combined in toluene (10 mL), water (5 mL) and EtOH (2.5 mL) and warmed to 95 °C in a sealed tube for 16 hours. The cooled mixture was filtered and the filtrate partitioned between water (30 mL) and EtOAc (30 mL). The aqueous layer was extracted with EtOAc (2 x 20 mL) and the combined organic phases were washed with brine (20 mL), dried over Na2S04, filtered and concentrated in vacuo. The residue was purified by silica column chromatography eluting with 2percent MeOH/DCM to afford the title compound (504 mg, 59percent yield) as a yellow foam. MS (apci) m/z = 281.2 (M+H).
59% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; at 95℃; for 16h;Sealed tube; Intermediate 8 5-(5-amino-4-methyl- 1 -phenyl- 1 FI-pyrazol-3-yl)- 1 -methylpyridin-2(1 H)-one (006691 3-Bromo-4-methyl-l-phenyl-1H-pyrazol-5-amine [Intermediate 7] (763 mg, 3.03 mmol), 1 -methyl-5-(4,4,5 ,5-tetramethyl- 1,3 ,2-dioxaborolan-2-yl)pyridin-2( 1 H)one (1.42 g, 6.05 mmol), K2C03 (1.67 g, 12.1 mmol) and Pd(PPh3)4 (350 mg, 0.30 mmol) were combined in toluene (10 mL), water (5 mL) and EtOH (2.5 mL) and warmed to 95 °C in a sealed tube for 16 hours. The cooled mixture was filtered and the filtrate partitioned between water (30 mL) and EtOAc (30 mL). The aqueous layer was extracted with EtOAc (2 x 20 mL) and the combined organic phases were washed with brine (20 mL), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica column chromatography eluting with 2percent MeOFI/DCM to afford the title compound (504 mg, 59percent yield) as a yellow foam. MS (apci) mz = 281.2 (M+H).
59% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; at 95℃; for 16h;Sealed tube; 3-bromo-4-methyl-l-phenyl-lH-pyrazol-5-amine (763 mg, 3.03 mmol), l-methyl-5- (4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyridin-2(lH)one (1.42 g, 6.05 mmol), K2C03 (1.67 g, 12.1 mmol) and Pd(PPh3)4 (350 mg, 0.30 mmol) were combined in toluene (10 mL), water (5 mL) and EtOH (2.5 mL) and warmed to 95 °C in a sealed tube for 16 hours. The cooled mixture was filtered and the filtrate partitioned between water (30 mL) and EtOAc (30 mL). The aqueous layer was extracted with EtOAc (2 x 20 mL) and the combined organic extracts were washed with brine (20 mL), dried over Na2S04, filtered and concentrated under vacuum. The residue was purified by silica column chromatography eluting with 2percent MeOH/DCM to afford the title compound (504 mg, 59percent yield) as a yellow foam. MS (apci) m/z = 281.2 (M+H).

 

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