Indole → HCID 5282533, compound

HRID 900737Notes

Reaction equation

HRID 900737 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

6

Reactant 5

HCID 798IndoleHCID 962WaterHCID 6212ChloroformHCID 516892Sodium BicarbonateHCID 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).

Workup

  1. customThe two layers were separated
  2. extractionthe aqueous phase was extracted with dichloromethane
  3. dry with materialThe combined organic extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash silica chromatography
  7. washeluting with 50% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-868f2bacc8ed465cae7cfc0a0f3a4840
Source dataset
uspto-grants-2008_04
Patent number
US07361660B2

Reaction notes

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