[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH2:9])[CH:4]=1.N1C=CC=CC=1.Cl[C:19]([O:21][C:22]([CH3:24])=[CH2:23])=[O:20]>C1COCC1>[F:11][C:2]([F:1])([F:10])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH:9][C:19](=[O:20])[O:21][C:22]([CH3:24])=[CH2:23])[CH:4]=14-(trifluoromethyl)pyridin-2-amine (1.0 g, 6.17 mmol) was dissolved in THF (20 mL) and treated with pyridine (600 μL, 7.4 mmol) and isopropenyl chloroformate (596 μL, 6.17 mmol). The reaction was stirred at rt for 6 h. The reaction was then concentrated and triturated with EtOAc. The crude residue was purified by MPLC (100% CH2Cl2) to yield a pale yellow solid (1.2 g, 79%); 1H-NMR (DMSO-d6) δ 11.0 (s, 1H), 8.57 (d, J=5.1 Hz, 1H), 8.10 (s, 1H), 7.45 (d, J=5.5 Hz, 1H), 4.81 (t, J=1.1 Hz, 1H), 4.76 (s, 1H), 1.94 (s, 3H).
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