C(C=P(CCCC)(CCCC)CCCC)#N.[Cl:17][C:18]1[N:19]=[C:20]([C:27]2[CH:48]=[CH:47][C:30]([O:31][CH2:32][CH2:33][CH:34]3[CH2:39][CH2:38][N:37]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:36][CH2:35]3)=[C:29]([C:49]([F:52])([F:51])[F:50])[CH:28]=2)[C:21]2[CH:26]=[CH:25][NH:24][C:22]=2[N:23]=1.[O:53]1[CH2:58][CH2:57][CH:56](O)[CH2:55][CH2:54]1>C1(C)C=CC=CC=1>[Cl:17][C:18]1[N:19]=[C:20]([C:27]2[CH:48]=[CH:47][C:30]([O:31][CH2:32][CH2:33][CH:34]3[CH2:39][CH2:38][N:37]([C:40]([O:42][C:43]([CH3:45])([CH3:44])[CH3:46])=[O:41])[CH2:36][CH2:35]3)=[C:29]([C:49]([F:50])([F:51])[F:52])[CH:28]=2)[C:21]2[CH:26]=[CH:25][N:24]([CH:56]3[CH2:57][CH2:58][O:53][CH2:54][CH2:55]3)[C:22]=2[N:23]=1Cyanomethylenetributylphosphorane (1.1 mL) was added to a mixture of tert-butyl 4-{2-[4-(2-chloro-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-2-(trifluoromethyl)phenoxy]ethyl}piperidine-1-carboxylate (1.0 g), tetrahydro-2H-pyran-4-ol (0.36 mL), and toluene (30 mL) at room temperature in a nitrogen atmosphere, and the reaction mixture was stirred overnight while heating to reflux. The reaction mixture was cooled to room temperature, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Hex:EtOAc=67:33 to 33:67), whereby tert-butyl 4-(2-{4-[2-chloro-7-(tetrahydro-2H-pyran-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-2-(trifluoromethyl)phenoxy}ethyl)piperidine-1-carboxylate (1.04 g) was obtained as a yellow amorphous material.
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