Ethyl chloroformate → HCID 57619241, compound

HRID 509987Notes

Reaction equation

HRID 509987 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12]2=[N:13][CH:14]=[C:15]([Cl:17])[CH:16]=[C:11]2[C:10]([CH2:18]N(C)C)=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:22]C(OCC)=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]([Cl:17])[CH:16]=[C:11]2[C:10]([CH2:18][Cl:22])=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 576192031H-Pyrrolo[2,3-b]pyridine-1-carboxylic acid, 5-chloro-3-[(dimethylamino)methyl]-, 1,1-dimethylethyl ester

Product 1

HCID 57619241HCID 57619241, compoundYield 39.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 5-chloro-3-dimethylaminomethyl-pyrrolo[2,3-b]pyridine-1-carboxylic acid tert-butyl ester (141, 4.20 g, 13.6 mmol) in 100 mL of toluene, ethyl chloroformate (1.48 mL, 15.5 mmol) was added under nitrogen. The reaction was stirred at room temperature for 2 hours, then concentrated under vacuum and combined with water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and the filtrate was concentrated under vacuum. The resulting material was purified by silica gel column chromatography eluting with 25% ethyl acetate in hexane to provide the desired compound (142, 1.60 g).

Workup

  1. concentrationconcentrated under vacuum
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under vacuum
  6. customThe resulting material was purified by silica gel column chromatography
  7. washeluting with 25% ethyl acetate in hexane

Sources & evidence

ORD record
ord-6c6e68c7889b4080a3e4562844effcd1
Source dataset
uspto-grants-2015_08
Patent number
US09096593B2

Reaction notes

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