Thioanisole → 6-(2-Aminomethylthiazol-4-yl)-3-(2,4-dichlorophenyl)-1,9-dimethyl-1,9-dihydropyrido[2,3-b]indol-2-one

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Reaction Steps

780 mg (1.3 mmol) of compound A {4-[3-(2,4-dichlorophenyl)-1,9-dimethyl-2-oxo-2,9-dihydro-1H-pyrido[2,3-b]indol-6-yl]thiazol-2-ylmethyl}carbamic acid benzyl ester are dissolved in 12 ml of trifluoroacetic acid. 8 ml (10.3 mmol) of thioanisole are added and the mixture is stirred at ambient temperature for 16 hours. It is poured into a saturated K2CO3 solution and the mixture is extracted with EtOAc. The organic phase is adsorbed onto silica and purification is carried out on a silica column, elution being carried out with EtOAc and then with 90/10/1 EtOAc/MeOH/NH3.

Provenance & Evidence