Dimethylformamide → HCID 57537482, Verbindung

Reaktionsgleichung

[Br:1][C:2]1[C:3](Cl)=[C:4]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[O:17][CH3:18])=[CH:9][N:8]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[C:5]2=[N:6][CH:7]=1.CO[CH:30]([OH:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[H-].[Na+].CN(C)[CH:42]=[O:43]>>[Br:1][C:2]1[C:3]([O:37][CH2:30][C:31]2[CH:32]=[CH:33][C:34]([O:43][CH3:42])=[CH:35][CH:36]=2)=[C:4]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[O:17][CH3:18])=[CH:9][N:8]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[C:5]2=[N:6][CH:7]=1

Komponenten

Edukt 4

HCID 6228Dimethylformamide

HCID 24758Sodium hydride

HCID 13736807HCID 13736807, Verbindung

HCID 57537472HCID 57537472, Verbindung

Produkt 1

HCID 57537482HCID 57537482, VerbindungAusbeute 74 %

Versuchsvorschrift

5-Bromo-4-chloro-3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine (245 mg, 0.52 mmol) and methoxybenzyl alcohol (723 mg, 5.2 mmol) were dissolved in dimethylformamide (0.25 mL). Sodium hydride (167 mg, 4.2 mmol) was added and the mixture was irradiated in a Personal Chemistry Optimizer at 120° C. for 5 min. The reaction was quenched with water, applied to a Varian chemelut cartridge and eluted with ethyl acetate. The crude product was purified by flash silica gel chromatography using a gradient of (ethyl acetate and methanol 9:1) in hexanes to afford 5-Bromo-4-(4-methoxy-benzyloxy)-3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine (220 mg, 0.38 mmol, 74% yield). 1H NMR (500 MHz, DMSO-d6) δ 8.39 (s, 1H), 7.66 (s, 1H), 7.40 (m, 1H), 7.35 (dd, J=7 Hz, J2=2 Hz, 1H), 7.08 (d, J=8 Hz, 1H), 7.01 (td, J1=7 Hz, J2=1 Hz, 1H), 6.77 (m, 4H), 5.63 (s, 2H), 4.37 (s, 2H), 3.71 (s, 3H), 3.64 (s, 3H), 3.58 (t, J=8 Hz, 1H), 0.83 (t, J=8 Hz, 1H), −0.08 (s, 9H). MS: m/z 569.4/571.3 (M+H+).