Tetrabutylammonium Fluoride → HCID 67202653, Verbindung
Reaktionsgleichung
C1(S([N:10]2[C:14]3[CH:15]=[N:16][C:17]([C:31]#[N:32])=[C:18]([CH2:19][CH:20]4[CH2:25][CH2:24][N:23]([CH2:26][C:27]([F:30])([F:29])[F:28])[CH2:22][CH2:21]4)[C:13]=3[C:12]3[CH:33]=[CH:34][CH:35]=[N:36][C:11]2=3)(=O)=O)C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>>[F:30][C:27]([F:28])([F:29])[CH2:26][N:23]1[CH2:22][CH2:21][CH:20]([CH2:19][C:18]2[C:13]3[C:12]4[CH:33]=[CH:34][CH:35]=[N:36][C:11]=4[NH:10][C:14]=3[CH:15]=[N:16][C:17]=2[C:31]#[N:32])[CH2:25][CH2:24]1Komponenten
3
Versuchsvorschrift
9-Benzenesulfonyl-5-[1-(2,2,2-trifluoroethyl)-piperidin-4-ylmethyl]-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (0.16 g, 0.3 mmol) was dissolved in tetrabutylammonium fluoride (1M in THF, 5 mL, 5 mmol) and stirred at ambient temperature for 24 h. The solution was filtered through 2 g NH2 cartridge, eluting with 1:1 methanol/dichloromethane. The filtrate was concentrated in vacuo and the residue diluted with water (10 mL) and the resultant precipitate collected by filtration. Purification of the solid by flash chromatography (silica, 5 g column, SPE Si-II, 0-6% methanol in DCM) afforded the title compound as a white solid (90 mg, 80%). 1H NMR (DMSO-D6, 400 MHz): 12.88 (s, 1H), 8.91 (s, 1H), 8.72-8.64 (m, 2H), 7.46 (dd, J=8.0, 4.8 Hz, 1H), 3.09 (q, J=10.3 Hz, 2H), 2.92-2.83 (m, 2H), 2.25-2.15 (m, 2H), 1.85-1.72 (m, 1H), 1.66-1.58 (m, 2H), 1.57-1.43 (m, 2H). LCMS (Method H): RT=9.20 min, M+H+=374.