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A mixture of 2.90 g, 19.07mMol of isocarbostyril and 14.40 g, 33.68mMol of phosphorus pentabromide were allowed to melt together at 140 °C. The melt turned into a red liquid and after about 10 minutes the reaction mixture solidified and was cooled. The reaction mixture was crushed up and dumped into ice water. The resulting solid was filtered and air-dried. wt. 5.50 g, 96percent yield, mp.=94-96°. Rf=0.66 in 40percent ethyl acetate in hexanes.
96%
at 140℃; for 0.166667 h;
Preparation of Intermediate A: A mixture of 2.90 g, 19.07mMol of isocarbostyril and 14.40 g, 33.68mMol of phosphorus pentabromide were allowed to melt together at 140 0C. The melt turned into a red liquid and after about 10 minutes the reaction mixture solidified and was cooled. The reaction mixture was crushed up and dumped into ice water. The resulting solid was filtered and air-dried, wt. 5.50 g, 96percent yield, mp.=94-96°. Rf=0.66 in 40percent ethyl acetate in hexanes.
71.3%
at 125 - 140℃;
In a 250ml three neck flask fitted with overhead stirrer and condenser which is also connected to a scrubber solution, 1-hydroxyisoquinoline (lO.g, 68.89mmol) and PBrs (53.38g, 124 mmol) were taken. The reaction mixture was gradually heated to 140°C. At about 125°C - 130°C the solid melts and a deep read solution obtained which on further heating converts to yellowish solid at ~135°C. The reaction mixture was heated at this temperature for lOmin then allowed to cool to room temperature. The pale yellow solid was crushed and added in portions into ice with stirring to obtain a pale yellow powder which was filtered and washed with water (150ml) and dried in an oven at 50°C under vacuum. The crude solid was purified by recrystallisation from EtOAc/heptane (14. lg, 99.93percent HPLC, 71.3percent yield). 1H-NMR (600MHz, CDCI3, TMS): S= 8.47 (s, 1H), 8.32(d, 1H), 8.19 (m, 1H), 7.72(m, 1H).
With N,N-dimethyl-formamide; phosphorus(V) oxybromide In dichloromethane at 0 - 25℃; for 6 h; Inert atmosphere
General procedure: The procedure is identical to general procedure I, except that reactions were conducted at 0.2 M concentration with N-oxide (1.00 equiv), POBr3 (3.00 equiv), DMF (1.50 equiv) at rt. 4.2 General procedure I for the bromination of azine N-oxides (0013) To a stirred solution of the appropriate azine N-oxides in anhydrous CH2Cl2 (0.1 M) at 0 °C is added POBr3 (1.2 equiv) followed by dropwise addition of DMF (0.5 equiv) under argon. The resulting reaction mixture was warmed to 25 °C and stirred for several hours until the reaction is complete as indicated by TLC. Saturated aqueous sodium carbonate solution is added to the reaction mixture slowly to adjust the pH to 7–8. The resulting mixture is separated and the aqueous phase is extracted with CH2Cl2 thoroughly. The organic phase is combined and washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to afford the crude product, which is purified by flash column chromatography using PE/EA (100:1) as eluent.
A mixture of 2.90 g, 19.07 mMol of isocarbostyril and 14.40 g, 33.68 mMol of phosphorus pentabromide were allowed to melt together at 140° C. The melt turned into a red liquid and after about 10 minutes the reaction mixture solidified and was cooled. The reaction mixture was crushed up and dumped into ice water. The resulting solid was filtered and air-dried. wt. 5.50 g, 96percent yield, mp.=94-96°. Rf=0.66 in 40percent ethyl acetate in hexanes.
With phosphorus pentabromide; at 140℃; for 0.166667h;Neat (no solvent);
A mixture of 2.90 g, 19.07 mMol of <strong>[491-30-5]isocarbostyril</strong> and 14.40 g, 33.68 mMol of phosphorus pentabromide were allowed to melt together at 140 C. The melt turned into a red liquid and after about 10 minutes the reaction mixture solidified and was cooled. The reaction mixture was crushed up and dumped into ice water. The resulting solid was filtered and air-dried. wt. 5.50 g, 96% yield, mp.=94-96. Rf=0.66 in 40% ethyl acetate in hexanes.
89%
With phosphorus pentabromide; at 140 - 145℃; for 0.166667h;
In a 50 ml. round-bottom flask, <strong>[491-30-5]isocarbostyril</strong> (0.50 g, 3.4 mmol) and phosphorus pentabromide (2.7 g, 9.8 mmol) were heated at 140-145 C for 10 min. The solid melted and lightened in color. The liquid solidified, and the reaction was stirred for an additional 10 min. On completion, the reaction mixture was cooled to room temperature, and ice/H20 (10 ml.) was poured into the flask. The solid precipitate was collected by filtration, washed with H20 (2 x 50 ml_), and dried under vacuum to obtain 860 mg (89% yield) of (1) as a buff-colored solid.
1,4-dibromo-2-methylisoquinolinium tetrafluoroborate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With hydrogen bromide;
5. The starting material was prepared by reaction of <strong>[1532-71-4]1-<strong>[1532-71-4]bromoisoquinoline</strong></strong> with HBr to give 1,4-di<strong>[1532-71-4]bromoisoquinoline</strong>, m.p. 95°-96°, followed by reaction of this compound with trimethyloxonium tetrafluoroborate in CH2 Cl2 to give 1,4-dibromo-2-methylisoquinolinium tetrafluoroborate; n.m.r. in solvent A: 3.5(s, 3H); 7.2-8.4(m, 5H).
With N,N-dimethyl-formamide; phosphorus(V) oxybromide; In dichloromethane; at 0 - 25℃; for 6.0h;Inert atmosphere;
General procedure: The procedure is identical to general procedure I, except that reactions were conducted at 0.2 M concentration with N-oxide (1.00 equiv), POBr3 (3.00 equiv), DMF (1.50 equiv) at rt. 4.2 General procedure I for the bromination of azine N-oxides (0013) To a stirred solution of the appropriate azine N-oxides in anhydrous CH2Cl2 (0.1 M) at 0 C is added POBr3 (1.2 equiv) followed by dropwise addition of DMF (0.5 equiv) under argon. The resulting reaction mixture was warmed to 25 C and stirred for several hours until the reaction is complete as indicated by TLC. Saturated aqueous sodium carbonate solution is added to the reaction mixture slowly to adjust the pH to 7-8. The resulting mixture is separated and the aqueous phase is extracted with CH2Cl2 thoroughly. The organic phase is combined and washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to afford the crude product, which is purified by flash column chromatography using PE/EA (100:1) as eluent.
N,N’-(isoquinoline-1,4-diyl)bis(4-fluorobenzenesulfonamide)[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine; In acetonitrile; at 70℃; for 7h;Inert atmosphere;
A round bottom flask was flame dried and back-flilled with Ar. Solids were weighed out (1 ,4 dibromo isoquinoline (1) (0.500 g, 1.74 mmol), <strong>[402-46-0]4-fluorobenzenesulfonamide</strong> (0.609 g, 3.48 mmol), Cul (0.132 g, 0.696 mmol), K2C03 (2.52 g, 18.27 mmol)) and added to flask.The flask was purged with Ar. MeCN (5 mL) and DMEDA (0.038 mL, 3.48 mmol) were then added to start reaction. Reaction was run at 70 C for 7 days. Upon completion, reaction was quenched by pouring mixture into ice/water (100 mL). EtOAc (3 x 50 mL) was used to extract the aqueous mixture. Combined organic layers were washed with water (50 mL) and brine (50 mL); dried (Na2S04); and evaporated to yield a crude product which, upon recrystallization using toluene (20 mL), yielded the title compound.