Water → HCID 59593276, compound

HRID 1256771Notes

Reaction equation

HRID 1256771 reaction equation
[C:1]([CH2:4][C:5](=[O:7])[CH3:6])(=[O:3])[CH3:2].[H-].[Na+].[C:10]([O:14][C:15]([N:17]1[C:21]2=[N:22][CH:23]=[CH:24][CH:25]=[C:20]2[C:19]([CH2:26]Cl)=[CH:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11].O>CS(C)=O>[C:10]([O:14][C:15]([N:17]1[C:21]2=[N:22][CH:23]=[CH:24][CH:25]=[C:20]2[C:19]([CH2:26][CH:4]([C:5](=[O:7])[CH3:6])[C:1](=[O:3])[CH3:2])=[CH:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 31261AcetylacetoneHCID 21463021tert-Butyl 3-(chloromethyl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate

Product 1

HCID 59593276HCID 59593276, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To acetylacetone (0.563 g, 5.62 mmol) in dimethyl sulfoxide (29.0 mL) was added sodium hydride (0.225 g, 60% in mineral oil, 5.62 mmol). After 20 minutes, 3-chloromethyl-pyrrolo[2,3-b]pyridine-1-carboxylic acid tert-butyl ester (512, 1.00 g, 3.75 mmol) was added to the reaction. The reaction was stirred at room temperature for 2 hours. The reaction was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 40% ethyl acetate in hexane to give a colorless oil (513, 0.59 g, 48.0%). MS (ESI) [M+H+]+=331.4.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. custompurified by silica gel column chromatography
  6. washeluting with 40% ethyl acetate in hexane
  7. customto give a colorless oil (513, 0.59 g, 48.0%)

Sources & evidence

ORD record
ord-8fa791cd40d741deb12fb0e1c72629f1
Source dataset
uspto-grants-2013_06
Patent number
US08461169B2

Reaction notes

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