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[ CAS No. 1221232-29-6 ]

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Chemical Structure| 1221232-29-6
Chemical Structure| 1221232-29-6
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Product Details of [ 1221232-29-6 ]

CAS No. :1221232-29-6 MDL No. :MFCD28661254
Formula : C9H5BrClN Boiling Point : -
Linear Structure Formula :- InChI Key :ClC1=CN=CC2=C1C=C(Br)C=C2
M.W :242.50 g/mol Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 1221232-29-6 ]

  • Downstream synthetic route of [ 1221232-29-6 ]

[ 1221232-29-6 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 669008-26-8 ]
  • [ 1221232-29-6 ]
  • N-(4-chloroisoquinolin-6-yl)-1-methylcyclopropane-1-sulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; potassium phosphate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In toluene; at 100℃; for 3h;Inert atmosphere; N-(4-chloroisoquinolin-6-yl)-<strong>[669008-26-8]1-methylcyclopropane-1-sulfonamide</strong> Into a 25-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen was added 6-bromo-4-chloroisoquinoline (200 mg, 0.82 mmol), <strong>[669008-26-8]1-methylcyclopropane-1-sulfonamide</strong> (223 mg, 1.65 mmol), K3PO4 (876 mg, 4.13 mmol), Pd2(dba)3*CHCl3 (86.0 mg, 0.08 mmol), Xantphos (144 mg, 0.25 mmol) and toluene (5 mL). The solution was stirred for 3 h at 100 C. and the reaction mixture was concentrated under vacuum. The residue was purified by silica gel column chromatography with ethyl acetate/petroleum ether (4:1). This resulted in 240 mg (98%) of N-(4-chloroisoquinolin-6-yl)-<strong>[669008-26-8]1-methylcyclopropane-1-sulfonamide</strong> as a yellow solid. [M+H]+ 297. Rt 1.05 min (method S).
  • 2
  • [ 2996-58-9 ]
  • [ 1221232-29-6 ]
  • 1-(4-chloroisoquinolin-6-yl)-4-methylpyrrolidin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
27% With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 100℃; for 3h; Inert atmosphere; 5.1 5.11 -(4-Chloroisoquinolin-6-yl)-4-methylpyrrolidin-2-one 5.1 1-(4-Chloroisoquinolin-6-yl)-4-methylpyrrolidin-2-one Into a 25 mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, were placed 6-bromo-4-chloroisoquinoline (50.0 mg, 0.21 mmol), 4-methylpyrrolidin-2-one (27.5 mg, 0.28 mmol), potassium phosphate (184 mg, 0.86 mmol), tris(dibenzylideneacetone)dipalladium(0) chloroform complex (19.7 mg, 0.02 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos, 16.7 mg, 0.03 mmol) and toluene (5 mL). The solution was stirred for 3 h at 100° C. The mixture was concentrated under vacuum. The residue was applied to a silica gel column with dichloromethane/methanol (100:1). This resulted in 23.9 mg (27%) of the title compound as a yellow solid.
  • 3
  • [ 13889-98-0 ]
  • [ 1221232-29-6 ]
  • 1-[4-(4-chloroisoquinolin-6-yl)piperazin-1-yl]ethan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In 1,4-dioxane at 100℃; for 2h; Sealed tube; 8.1 8.11 -[4-(4-Chloroisoquinolin-6-yl)piperazin- 1 -yl] ethan- i-one 8.1 1-[4-(4-Chloroisoquinolin-6-yl)piperazin-1-yl]ethan-1-one Into a 20 mL sealed tube, were placed 6-bromo-4-chloroisoquinoline (150 mg, 0.62 mmol), dioxane (10 mL), sodium tert-butoxide (72.0 mg, 0.75 mmol), (2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (7.00 mg, 0.01 mmol), tris(dibenzylideneacetone)dipalladium(0) (3.00 mg, 0.003 mmol) and 1-(piperazin-1-yl)ethan-1-one (80.0 mg, 0.62 mmol). The solution was stirred for 2 h at 100° C. in an oil bath and concentrated under vacuum. This resulted in 150 mg (84%) of the title compound as a yellow solid.
  • 4
  • [ 108-27-0 ]
  • [ 1221232-29-6 ]
  • 1-(4-chloroisoquinolin-6-yl)-5-methylpyrrolidin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 100℃; for 3h; Inert atmosphere; 12.1 12.11 -(4-chloroisoquinolin-6-yl)-5-methylpyrroli- din-2-one 12.1 1-(4-chloroisoquinolin-6-yl)-5-methylpyrrolidin-2-one Into a 50-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen were placed 6-bromo-4-chloroisoquinoline (161 mg, 0.66 mmol), 5-methylpyrrolidin-2-one (81.0 mg, 0.82 mmol), potassium phosphate (394 mg, 1.86 mmol), tris(dibenzylideneacetone)dipalladium(0) chloroform complex (32.1 mg, 0.03 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos, 35.7 mg, 0.06 mmol) and toluene (15 mL). The mixture was stirred for 3 h at 100° C. The reaction mixture was concentrated to dryness, redissolved in 20 mL of dichloromethane and washed with water (10 mL) and brine (10 mL). The organic phase was dried over sodium sulfate, filtered and concentrated to dryness. The residue was purified by silica gel chromatography (petrol ether/ethyl acetate). This resulted in 165 mg (73%) of the title compound as a light yellow solid.
  • 5
  • [ 1221232-29-6 ]
  • [ 145214-05-7 ]
  • 2-(4-chloroisoquinolin-6-yl)oxazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; at 100℃; for 11h; Example 25 2-(4-(4-(1-methyl-1H-pyrazol-4-yl)phenyl)isoquinolin-6-yl)oxazole (119) 2-(4-chloroisoquinolin-6-yl)oxazole To 6-bromo-4-chloroisoquinoline (109 mg, 0.449 mmol) and Pd(PPh3)4 (26.0 mg, 0.022 mmol) in a microwave vial were added degassed 1,4-dioxane (1.80 mL) and <strong>[145214-05-7]2-(tributylstannyl)oxazole</strong> (206 μl, 0.674 mmol). The reaction mixture was heated in an oil bath at 100 C. for 11 h before being concentrated. The crude was purified via biotage column chromatography (dichloromethane/ethyl acetate 95/5 to 50/50) to give the title compound (65 mg, 63% yield).
  • 6
  • [ 590418-04-5 ]
  • [ 1221232-29-6 ]
  • 4-chloro-6-(3-methyl-4-nitrophenyl)isoquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,2-dimethoxyethane; water at 50℃; for 4h; 060.1 Step 1: 4-chloro-6-(3-methyl-4-nitrophenyl)isoquinoline Na2C03(524.5 mg, 4.95 mmol, 2 equiv) and Pd(dppf)Cl2 (181.0 mg, 0.25 mmol, 0.1 equiv) were added to a solution of 6-bromo-4-chloroisoquinoline (600 mg, 2.47 mmol, 1 equiv) and 4,4,5, 5-tetramethyl-2-(3-methyl-4-nitrophenyl)-l,3,2-dioxaborolane (976.4 mg, 3.71 mmol, 1.5 equiv) in DME (6 ml) and water (1.5 mL). The mixture was stirred at 50 °C for four hours. Volatiles were removed under reduced pressure and the residue was purified by silica gel column chromatography with petroleum ether/ethyl acetate (10: 1) to afford the desired final product as a brown solid (700mg, 95%)
95% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,2-dimethoxyethane; water at 50℃; for 4h; 60.1 Step 1: 4-chloro-6-(3-methyl-4-nitrophenyl)isoquinoline Na2C03(524.5 mg, 4.95 mmol, 2 equiv) and Pd(dppf)Ch (181.0 mg, 0.25 mmol, 0.1 equiv) were added to a solution of 6-bromo-4-chloroisoquinoline (600 mg, 2.47 mmol, 1 equiv) and 4,4,5,5-tetramethyl-2-(3-methyl-4-nitrophenyl)-l,3,2-dioxaborolane (976.4 mg, 3.71 mmol, 1.5 equiv) in DME (6 ml) and water (1.5 mL). The mixture was stirred at 50 °C for four hours. (1195) Volatiles were removed under reduced pressure and the residue was purified by silica gel column chromatography with petroleum ether/ethyl acetate (10: 1) to afford the desired final product as a brown solid (700mg, 95%)
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