Water → HCID 57619358, compound

HRID 1256848Notes

Reaction equation

HRID 1256848 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12]2=[N:13][CH:14]=[C:15]([C:17]#[N:18])[CH:16]=[C:11]2[C:10]([CH2:19]N(C)C)=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:23]C(OCC)=O.O>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[C:12]2=[N:13][CH:14]=[C:15]([C:17]#[N:18])[CH:16]=[C:11]2[C:10]([CH2:19][Cl:23])=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 10928Ethyl chloroformateHCID 57619406HCID 57619406, compound

Product 1

HCID 57619358HCID 57619358, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 5-cyano-3-dimethylaminomethyl-pyrrolo[2,3-b]pyridine-1-carboxylic acid tert-butyl ester (634, 2.60 g, 8.66 mmol) in toluene (60.0 mL) under an atmosphere of nitrogen was added ethyl chloroformate (0.828 mL, 8.66 mmol). The reaction was stirred at room temperature for 3 hours, then 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 20% to 100% ethyl acetate in hexane to give a white solid (635, 400 mg, 16%).

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 20% to 100% ethyl acetate in hexane
  7. customto give a white solid (635, 400 mg, 16%)

Sources & evidence

ORD record
ord-893806f494e14d2e9451bb92d933a4fe
Source dataset
uspto-grants-2013_06
Patent number
US08461169B2

Reaction notes

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