1-Chloroethyl chloroformate → HCID 9976793, compound

HRID 1828233Notes

Reaction equation

HRID 1828233 reaction equation
C([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH2:13][N:14]1[C:18]2=[N:19][CH:20]=[CH:21][CH:22]=[C:17]2[C:16]([S:23]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[CH:27]=2)(=[O:25])=[O:24])=[CH:15]1)C1C=CC=CC=1.ClC(OC(Cl)=O)C>ClCCCl>[Cl:32][C:28]1[CH:27]=[C:26]([S:23]([C:16]2[C:17]3[C:18](=[N:19][CH:20]=[CH:21][CH:22]=3)[N:14]([CH2:13][CH:9]3[CH2:10][CH2:11][CH2:12][NH:8]3)[CH:15]=2)(=[O:25])=[O:24])[CH:31]=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 10412212HCID 10412212, compound

Product 1

HCID 9976793HCID 9976793, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A stirred solution of 1-[(1-benzyl-pyrrolidin-2-yl)methyl]-3-(3-chlorophenyl-sulfonyl)-1H-pyrrolo[2,3-b]pyridine (0.812 g, 1.74 mmol) in 1,2-dichloroethane under a nitrogen atmosphere is treated with 1-chloroethylchloroformate (0.47 mL, 4.35 mmol); heated at reflux temperature until the disappearance of starting material by thin layer chromatography (3 h), cooled and concentrated in vacuo. The resultant residue is dissolved in CH2Cl2 and re-evaporated twice. This residue is dissolved in ethanol, heated at reflux temperature for 1.5 h, cooled to room temperature, diluted with water, and extracted with ethyl acetate. The extracts are combined, washed sequentially with water and brine, and concentrated in vacuo. The final residue is purified by flash column chromatography (10–15% methanol in CH2Cl2 as eluent) to afford the title compound as an oil, 443 mg (68% yield), identified by HNMR and mass spectral analyses.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature until the disappearance of starting material by thin layer chromatography (3 h)
  3. temperaturecooled
  4. concentrationconcentrated in vacuo
  5. dissolutionThe resultant residue is dissolved in CH2Cl2
  6. customre-evaporated twice
  7. dissolutionThis residue is dissolved in ethanol
  8. temperatureheated
  9. temperatureat reflux temperature for 1.5 h
  10. additiondiluted with water
  11. extractionextracted with ethyl acetate
  12. washwashed sequentially with water and brine
  13. concentrationconcentrated in vacuo
  14. customThe final residue is purified by flash column chromatography (10–15% methanol in CH2Cl2 as eluent)

Sources & evidence

ORD record
ord-eb2fd63718cf435ba0c61b56f1ab255d
Source dataset
uspto-grants-2006_06
Patent number
US07057039B2

Reaction notes

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