Indole → HCID 5282533, compound

Reaction equation

ClC1N=C(C)N([CH2:8][C:9]2[S:24][C:12]3[N:13]([CH2:20][CH:21]([CH3:23])[CH3:22])[C:14](=[O:19])[N:15]([CH3:18])[C:16](=[O:17])[C:11]=3[C:10]=2C(N(OC)C)=O)C=1Cl.[NH:32]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=[CH:33]1.[C:41](=[O:44])([O-])[OH:42].[Na+].O.[CH:47](Cl)(Cl)Cl>>[NH:32]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:34]([CH2:8][C:9]2[S:24][C:12]3[N:13]([CH2:20][CH:21]([CH3:22])[CH3:23])[C:14](=[O:19])[N:15]([CH3:18])[C:16](=[O:17])[C:11]=3[C:10]=2[C:41]([O:42][CH3:47])=[O:44])=[CH:33]1

Participants

Reactant 5

HCID 798Indole

HCID 962Water

HCID 6212Chloroform

HCID 516892Sodium Bicarbonate

HCID 10184774HCID 10184774, compound

Product 1

HCID 5282533HCID 5282533, compound

Procedure

The product from example 1 part b) (2.5 g) was dissolved in chloroform (20 ml), then indole (1.08 g), sodium hydrogen carbonate (1.4 g) and water (20 ml) were added and the reaction mixture was stirred at room temperature for 3 days. The two layers were separated and the aqueous phase was extracted with dichloromethane. The combined organic extracts were dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by flash silica chromatography eluting with 50% ethyl acetate in isohexane to give the sub-title compound as a white solid (1.8 g).