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Chemical Structure| 22282-80-0 Chemical Structure| 22282-80-0

Structure of 22282-80-0

Chemical Structure| 22282-80-0

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Product Details of [ 22282-80-0 ]

CAS No. :22282-80-0
Formula : C7H8ClN
M.W : 141.60
SMILES Code : CC1=CN=C(C)C=C1Cl
MDL No. :MFCD18415680
InChI Key :PKEAPXXPQSPHFU-UHFFFAOYSA-N
Pubchem ID :22660266

Safety of [ 22282-80-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H320-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 22282-80-0 ]

* 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 [ 22282-80-0 ]

[ 22282-80-0 ] Synthesis Path-Downstream   1~3

  • 2
  • [ 827614-64-2 ]
  • [ 22282-80-0 ]
  • 2',5'-dimethyl-[3,4'-bipyridin]-6-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.17 g With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; at 80.0℃; for 20.0h; [00214] The title compound (0.17 g) was prepared from 4-chloro-2,5-dimethyl-pyridine (0.50 g, 3.5 mmol, CAS: 22282-80-0), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (0.78 g, 3.5 mmol, CAS: 827614-64-2), Pd(dppf)Cl2 (0.26 g, 0.35 mmol) and sodium carbonate (1.1 g, 10.6 mmol) in accordance with the procedure described for Intermediate 1.1, heating at 80C for 20 h. The crude product was purified by flash column chromatography on the Biotage Isolera OneTM (10 g silica column, eluting 0 - 5% MeOH in DCM) and an SCX cartridge (5 g, washed with MeOH and eluted with 2 M methanolic ammonia).1H NMR (400 MHz, DMSO-d6) δ: 8.29 (s, 1H), 7.96 (d, 1H), 7.47 (dd, 1H), 7.07 (s, 1H), 6.52 (dd, 1H), 6.15 (br s, 2H), 2.43 (s, 3H), 2.22 (s, 3H).
0.17 g With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In 1,4-dioxane; water; at 80.0℃; for 20.0h;Microwave irradiation; General procedure: [00192] To a stirred suspension of 4-chloro-3,5-dimethyl-pyridine (0.40 g, 2.8 mmol, CAS: 143798-73-6), 4-aminophenylboronic acid hydrochloride (0.59 g, 3.4 mmol, CAS: 80460-73-7) and sodium carbonate (0.96 g, 9.0 mmol) in degassed water (8 mL) and 1,4-dioxane (8 mL) was added Pd(dppf)CI2 (0.21 g, 0.28 mmol) and then heated by microwave irradiation at 120C for 2 h. The reaction mixture was filtered through a pad of Celite and rinsed with EtOAc. The filtrate was washed with brine, dried over MgS04, filtered and concentrated in vacuo. The crude product was purified by flash column chromatography (eluting 10 - 30% EtOAc in DCM) to provide the title compound (0.15 g). LCMS (Method 3): 1.42 min, 199.1 [M+H]+
0.17 g With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In 1,4-dioxane; water; at 80.0℃; for 20.0h;Microwave irradiation; General procedure: [00192] To a stirred suspension of 4-chloro-3,5-dimethyl-pyridine (0.40 g, 2.8 mmol, CAS: 143798-73-6), 4-aminophenylboronic acid hydrochloride (0.59 g, 3.4 mmol, CAS: 80460-73-7) and sodium carbonate (0.96 g, 9.0 mmol) in degassed water (8 mL) and 1,4-dioxane (8 mL) was added Pd(dppf)CI2 (0.21 g, 0.28 mmol) and then heated by microwave irradiation at 120C for 2 h. The reaction mixture was filtered through a pad of Celite and rinsed with EtOAc. The filtrate was washed with brine, dried over MgS04, filtered and concentrated in vacuo. The crude product was purified by flash column chromatography (eluting 10 - 30% EtOAc in DCM) to provide the title compound (0.15 g). LCMS (Method 3): 1.42 min, 199.1 [M+H]+
  • 3
  • [ 819057-45-9 ]
  • [ 22282-80-0 ]
  • 4-(2,5-dimethylpyridin-4-yl)-3-fluoroaniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.29 g With chloro‐(2‐dicyclohexylphosphino‐2′,4′,6′‐triisopropyl‐1,1′‐biphenyl)‐2‐(2′‐amino‐1,1′‐biphenyl)palladium(II); potassium carbonate; In ethanol; water; at 80.0℃; for 6.0h; General procedure: [00189] To a solution of (3-methoxy-4-pyridyl)boronic acid (0.7 g, 4.6 mmol, CAS: 1008506-24-8), 4-iodoaniline (1.0 g, 4.6 mmol, CAS: 540-37-4) and potassium phosphate (2.9 g, 13 mmol) in water (7 mL) and ethanol (7 mL) was added XPhos Pd G2 (1.8 g, 0.23 mmol) and the reaction heated to 80C for 6 h. The reaction mixture was diluted with water and the crude product extracted into EtOAc. The combined organics were washed with water, brine, dried over Na2SO4 filtered and concentrated in vacuo. The crude product was purified by flash column chromatography (eluting 50% EtOAc in heptanes) to provide the title compound (0.25 g). LCMS (Method 2): 0.54 min, 201.1 [M+H]+
0.29 g With chloro‐(2‐dicyclohexylphosphino‐2′,4′,6′‐triisopropyl‐1,1′‐biphenyl)‐2‐(2′‐amino‐1,1′‐biphenyl)palladium(II); potassium carbonate; In ethanol; water; at 80.0℃; for 6.0h; General procedure: [00189] To a solution of (3-methoxy-4-pyridyl)boronic acid (0.7 g, 4.6 mmol, CAS: 1008506-24-8), 4-iodoaniline (1.0 g, 4.6 mmol, CAS: 540-37-4) and potassium phosphate (2.9 g, 13 mmol) in water (7 mL) and ethanol (7 mL) was added XPhos Pd G2 (1.8 g, 0.23 mmol) and the reaction heated to 80C for 6 h. The reaction mixture was diluted with water and the crude product extracted into EtOAc. The combined organics were washed with water, brine, dried over Na2SO4 filtered and concentrated in vacuo. The crude product was purified by flash column chromatography (eluting 50% EtOAc in heptanes) to provide the title compound (0.25 g). LCMS (Method 2): 0.54 min, 201.1 [M+H]+
 

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