1,2,3,4,5-pentafluoro-6-isocyanatobenzene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of pentafluorophenyl isocyanate (0.03 mL, 0.23 mmol) and iPr2NEt (0.05 mL, 0.29 mmol) in DMF (1 mL), a hot solution of 7-chloro-4-(1-piperazinyl)-2-quinolinamine (50 mg, 0.19 mmol) in DMF (2 mL) was added. After stirring at rt overnight, the mixture was poured into ice-water. The solid was collected by filtration and re-dissolved in CH2Cl2-MeOH, then purified by preparative TLC (CH2Cl2-MeOH, 9:1) affording the product as a light yellow solid. LC-MS: 472 (M++1). 1HNMR (DMSO-d6) δ 3.02 (br.s, 4H), 3.70 (br.s, 4H), 6.28 (s, 1H), 6.50 (s, 2H), 7.10 (d, 1H), 7.39 (s, 1H), 7.78 (d, 1H), 8.80 (s, 1H). The solid was collected by filtration re-dissolved in CH2Cl2-MeOH purified by preparative TLC (CH2Cl2-MeOH, 9:1)