Reaktion #428472

Reaktionsgleichung

4-(3-chloro-9-(benzenesulfonyl)-9H-pyrido[2,3-b]indol-6-yl)phenol

triphenylphosphine

3-(diethylamino)propan-1-ol

diisopropyldiazodicarboxylate

→

3-(4-(3-chloro-9-(benzenesulfonyl)-9H-pyrido[2,3-b]indol-6-yl)phenoxy)-N,N-diethylpropan-1-amine

Ausbeute 51.2%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenconcentrated under reduced pressure
2. 2
   SonstigeThe crude residue was chromatographed over silica gel column (
3. 3
   Wascheneluted with mixtures of AcOEt and EP
4. 4
   workup.DISSOLUTIONThe product was then dissolved in dichloromethane
5. 5
   Sonstigeprecipitated with EP
6. 6
   FiltrationThe solid was then filtered
7. 7
   Waschenwashed with EP

Vorschrift

To a solution of 4-(3-chloro-9-(benzenesulfonyl)-9H-pyrido[2,3-b]indol-6-yl)phenol (180 mg, 0.41 mmol, 1 eq.), triphenylphosphine (430 mg, 1.64 mmol, 4 eq.) and 3-(diethylamino)propan-1-ol (264 mg, 2.05 mmol, Seq.) in THF (10 ml) was added diisopropyldiazodicarboxylate (DIAD, 332 mg, 1.64 mmol, 4 eq.). The resulting solution was stirred at room temperature under Ar for 20 h and concentrated under reduced pressure. The crude residue was chromatographed over silica gel column (eluted with mixtures of AcOEt and EP and then AcOEt and MeOH). The product was then dissolved in dichloromethane and precipitated with EP. The solid was then filtered and washed with EP to give 3-(4-(3-chloro-9-(benzenesulfonyl)-9H-pyrido[2,3-b]indol-6-yl)phenoxy)-N,N-diethylpropan-1-amine (113 mg, 0.21 mmol, 51% yield). 1H NMR (CDCl3 300 MHz) δ ppm 8.47 (dd, 2H, J=2.6 Hz, 8.3 Hz), 8.18 (d, 1H, J=2.3 Hz), 8.13 (d, 2H, J=7.4 Hz), 8.01 (d, 1H, J=1.5 Hz), 7.77 (dd, 1H, J=1.8 Hz, 8.7 Hz), 7.54 (dd, 3H, J=8.7 Hz, 9.0 Hz), 7.42 (dd, 2H, J=7.3 Hz, 7.9 Hz), 7.01 (d, 2H, J=8.6 Hz), 4.08 (t, 2H, J=6.1 Hz), 2.58-2.72 (m, 6H), 2.00 (dd, 2H, J=6.8 Hz, 7.5 Hz), 1.08 (t, 6H, J=7.2 Hz). NMR 13C 75 MHz CDCl3 δ ppm 162.5 (C), 158.9 (C), 149.3 (C), 145.6 (CH), 138.6 (C), 137.5 (C), 137.4 (C), 134.3 (CH), 129.1 (2×CH), 128.3 (2×CH), 128.3 (C), 128.1 (CH), 127.6 (2×CH), 122.4 (C), 120.1 (C), 118.8 (CH), 115.5 (CH), 115.1 (2×CH), 66.5 (CH2), 49.5 (CH2), 47.1 (2×CH2), 26.8 (CH2), 11.6 (2×CH3). MS [ESI] 548 [M+H 35Cl], 550 [M+H 37Cl].

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