Water → HCID 59593276, compound

HRID 1952083Notes

Reaction equation

HRID 1952083 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-17209df283614ee395f89469c2aba993
Source dataset
uspto-grants-2013_03
Patent number
US08404700B2

Reaction notes

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