8-Hydroxyquinoline → HCID 11489278, compound

Participants

Reaction Steps

[7-Fluoro-5-methyl-1-oxo-2-(2-trimethylsilanyl-ethoxymethyl)-1,2-dihydro-isoquinolin-6-yl]-methyl-carbamic acid tert-butyl ester (44 mg, 0.10 mmol, Example 119) was treated with TFA for 1 h and concentrated in vacuo. Treatment of this crude material with 25 mg (0.115 mmol) of p-iodoaniline, 4 mg of CuI, 3 mg 8-hydroxyquinoline and 17 mg of K2CO3 in 200 μL of DMSO at 120° C. for 18 hrs, after which the reaction was cooled to room temperature, diluted with ethyl acetate and washed with brine. The combined organic layers were dried over Na2SO4 and concentrated in vacuo to give a crude residue, which was subjected to coupling with 57 mg of (5-Chloro-thiophene-2-sulfonyl)-carbamic acid ethyl ester as described in Example 13, gave 10 mg of 5-chloro-N-[({4-[7-fluoro-5-methyl-6-(methylamino)-1-oxoisoquinolin-2(1H)-yl]phenyl}amino)carbonyl]thiophene-2-sulfonamide after RP-HPLC purification. ES-MS (M+H)+=521.1 (Cl).

Provenance & Evidence