Ethyl Acetate → HCID 68428015, compound

HRID 642411Notes

Reaction equation

HRID 642411 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([O:22][C:23](=[O:25])[CH3:24])=[C:8]2[CH:16]=[CH:15][N:14]([CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20])[C:9]2=[C:10]([C:12]#[N:13])[N:11]=1)=[O:5])[CH3:2].[Cl:26]N1C(=O)CCC1=O.C(OCC)(=O)C>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:7]([O:22][C:23](=[O:25])[CH3:24])=[C:8]2[C:16]([Cl:26])=[CH:15][N:14]([CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20])[C:9]2=[C:10]([C:12]#[N:13])[N:11]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 31398ChlorosuccinimideHCID 68426174HCID 68426174, compound

Product 1

HCID 68428015HCID 68428015, compoundYield 55.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-acetoxy-7-cyano-1-(3-methyl-butyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester (0.44 g, 1.28 mmol) and N-chlorosuccinimide (0.188 g, 1.41 mmol) in 8 mL of N,N′-dimethylformamide was heated at 100° C. for 1 h. Ethyl acetate (100 mL) was added. The organic solution was washed with water, dried over anhydrous sodium sulfate, and concentrated. The crude produce was purified by flash chromatography from silica gel with a gradient of 0-40% ethyl acetate in hexanes to afford 0.27 g of the title compound as a white solid. MS: (+) m/z 378.3 (M+1).

Workup

  1. washThe organic solution was washed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThe crude produce
  5. customwas purified by flash chromatography from silica gel with a gradient of 0-40% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-2b74e7640f564b8cb6a1a56e87fa8afe
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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