Dimethylformamide → HCID 19876062, Verbindung

Reaktionsgleichung

[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH2:10][N:11]3[C:15]4=[N:16][C:17]([CH3:21])=[CH:18][C:19]([CH3:20])=[C:14]4[N:13]=[C:12]3[CH2:22][CH3:23])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].[C:26]12[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=1)NC(=O)O[C:27]2=[O:28].C[N:39]([CH:41]=[O:42])C>>[C:41]([C:36]1[CH:35]=[CH:34][CH:33]=[CH:32][C:26]=1[C:27]([N:1]1[C:9]2[C:4](=[CH:5][C:6]([CH2:10][N:11]3[C:15]4=[N:16][C:17]([CH3:21])=[CH:18][C:19]([CH3:20])=[C:14]4[N:13]=[C:12]3[CH2:22][CH3:23])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1)=[O:28])(=[O:42])[NH2:39]

Komponenten

Edukt 4

HCID 6228Dimethylformamide

HCID 8359Isatoic Anhydride

HCID 24758Sodium hydride

HCID 100407273-(5-indolyl)methyl-5,7-dimethyl-2-ethyl-3H-imidazo[4,5-b]pyridine

Produkt 1

HCID 19876062HCID 19876062, VerbindungAusbeute 77 %

Versuchsvorschrift

To a solution of the product of Example 2, Step A (200 mg, 0.66 mmol) in 7 mL of DMF was added NaH (53 mg, 1.23 mmol) and the mixture stirred for a few minutes. Isatoic anhydride (160 mg, 0.99 mmol) was added to the reaction mixture and it was stirred for 16 hours. The solvent was removed in vacuo and the resultant residue was flash column chromatographed with 15% of (10/1) mixture of MeOH/NH4OH in CHCl3 to give titled compound (236 mg, 77%).