CC1C=CC(S(O[CH2:12][CH2:13][O:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][NH:23][C:24]([C:26]3[C:27]([CH3:36])=[N:28][C:29]4[C:34]([CH:35]=3)=[CH:33][CH:32]=[CH:31][N:30]=4)=[O:25])=[CH:18][C:17]=2[F:37])(=O)=O)=CC=1.C1N2CCOCCOCCN(CCOCCOCC2)CCOCCOC1.[F-:64].[K+]>CC#N.O>[F:37][C:17]1[CH:18]=[C:19]([CH2:22][NH:23][C:24]([C:26]2[C:27]([CH3:36])=[N:28][C:29]3[C:34]([CH:35]=2)=[CH:33][CH:32]=[CH:31][N:30]=3)=[O:25])[CH:20]=[CH:21][C:16]=1[CH2:15][O:14][CH2:13][CH2:12][F:64]A flask with a solution of 19 mg 2-[[2-fluoro-4-[[(2-methyl-1,8-naphthyridine-3-carbonyl)amino]methyl]phenyl]methoxy]ethyl 4-methylbenzenesulfonate (0.036 mmol), 26 mg Kryptofix 222 (4,7,13,16,21,24-Hexaoxa-1,10-diazabicyclo[8.8.8]-hexacosane) (0.069 mmol) and 4 mg KF (0.069 mmol) in 1.0 ml dry MeCN was added to a preheated oil bath and heated at 90 C for 30 min. The reaction mixture was cooled to room temperature and diluted with water. The mixture was extracted twice with EtOAc. The combined organic phases were washed with brine, dried (MgSO4) and concentrated. Flash chromatography gave 9.6 mg (72%).
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