4-Chloroisoquinoline

General procedure: To an 8 mL dram vial was added iodobenzene diacetate (0.6 mmol, 1.5 equiv), and heteroarene(0.4 mmol, 1 eq.), anhydrous dichloroethane (1 mL), then chloride source (5 equiv). The solutionwas allowed to stir (1000 rpm) at 50 °C for the indicated amount of time. After which the solutionwas washed with saturated sodium bicarbonate, followed by saturated sodium thiosulfate andconcentrated. The crude mixture was then purified by column chromatography.General procedure: 2 mol% Pd(OAc)2/3 mol% Nixantphos, anhydrous DMF (1.0 ml) were added to an oven-dried 10 ml reaction vial equipped with a stir bar, the mixture was stirred at 45 C under an argon atmosphere for 1h to be a dark brown solution. 1 mol% CuI/1.1 mol% Nixantphos, anhydrous DMF (1.0 ml) were added to an oven-dried 10 ml reaction vial equipped with a stir bar, the mixture was stirred at 60 C under an argon atmosphere for 2h to be a colorless transparent solution. The amount of catalyst and solvent should scaled up by the number of reactions. Benzoxazoles (0.25 mmol), aryl chlorides (0.3 mmol) and K3PO4*7H2O (42.3 mg, 0.125 mmol, 0.5 equiv) were added to an oven-dried 10 ml reaction vial equipped with a stir bar. A stock solution of Pd(OAc)2/Nixantphos and CuI/Nixantphos in 1 ml of dry DMF was taken up by syringe and added to the reaction vial. The reaction vial filled with argon was then sealed with a septum. The reaction mixture was stirred for12 h or 24 h at 120 C, quenched with two drops of H2O, diluted with 3 mL of ethyl acetate, and filtered over a pad of MgSO4 and silica. The pad was rinsed with additional ethyl acetate, and the solution was concentrated in vacuo. The crude material was loaded onto a silica gel column and purified by flash chromatography.General procedure: To an 8 mL dram vial was added iodobenzene diacetate (0.6 mmol, 1.5 equiv), and heteroarene(0.4 mmol, 1 eq.), anhydrous dichloroethane (1 mL), then chloride source (5 equiv). The solutionwas allowed to stir (1000 rpm) at 50 C for the indicated amount of time. After which the solutionwas washed with saturated sodium bicarbonate, followed by saturated sodium thiosulfate andconcentrated. The crude mixture was then purified by column chromatography.

Molecular Weight:163.60
XLogP3:2.7
Hydrogen Bond Acceptor Count:1
Exact Mass:163.0188769
Monoisotopic Mass:163.0188769
Topological Polar Surface Area:12.9
Heavy Atom Count:11
Complexity:138
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes