Dimethylformamide → ethyl ((1S)-5-{3-[[6-(4-ethylphenyl)-3-(trifluoromethyl)-2-pyridinyl](methyl)amino]propoxy}-2,3-dihydro-1H-inden-1-yl)acetate

Reaktionsgleichung

[H-].[Na+].[CH2:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:16]=[C:15]([NH:17][CH2:18][CH2:19][CH2:20][O:21][C:22]3[CH:23]=[C:24]4[C:28](=[CH:29][CH:30]=3)[C@H:27]([CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:26][CH2:25]4)[C:14]([C:37]([F:40])([F:39])[F:38])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)[CH3:4].[CH3:41]N(C=O)C>>[CH2:3]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[N:16]=[C:15]([N:17]([CH3:41])[CH2:18][CH2:19][CH2:20][O:21][C:22]3[CH:23]=[C:24]4[C:28](=[CH:29][CH:30]=3)[C@H:27]([CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:26][CH2:25]4)[C:14]([C:37]([F:40])([F:38])[F:39])=[CH:13][CH:12]=2)=[CH:9][CH:10]=1)[CH3:4]

Komponenten

Edukt 3

HCID 6228Dimethylformamide

HCID 24758Sodium hydride

HCID 59300466HCID 59300466, Verbindung

Produkt 1

HCID 59300427ethyl ((1S)-5-{3-[[6-(4-ethylphenyl)-3-(trifluoromethyl)-2-pyridinyl](methyl)amino]propoxy}-2,3-dihydro-1H-inden-1-yl)acetateAusbeute 8 %

Versuchsvorschrift

Sodium hydride (0.02 g, 0.86 mmol) was added to a solution of ethyl [(1 S)-5-(3-{[6-(4-ethylphenyl)-3-(trifluoromethyl)-2-pyridinyl]amino}propoxy)-2,3-dihydro-1H-inden-1-yl]acetate (Example 318) (0.21 g, 0.39 mmol) in DMF (2 mL). After stirring at rt for 30 min, Mel (0.05 mL, 6.32 mmol) was added. The mixture was stirred at rt for 18 h, quenched with water (5 mL), and extracted with ether (3×). The combined ether extracts were washed with water and brine, dried (MgSO4), filtered, and concentrated under reduced pressure. The product (0.017 g, 8%) was isolated after silica gel flash chromatography (2:1 hexanes/EtOAc). 1H NMR (400 MHz, CD2Cl2) δ 7.99 (d, 2H), 7.85 (d, 1H), 7.35-7.25 (m, 3H), 7.01 (d, 1H), 6.72 (d, 1H), 6.65 (dd, 1H), 4.15 (q, 2H), 4.00 (t, 2H), 3.73 (t, 2H), 3.47 (qt, 1H), 3.08 (s, 3H), 2.90-2.68 (m, 5H), 2.42-2.30 (m, 2H), 2.15 (qt, 2H), 1.78-1.68 (m, 1H), 1.32-1.26 (m, 6H).