1-Chloro-4-(chloromethyl)benzene → HCID 59754773, compound

HRID 751444Notes

Reaction equation

HRID 751444 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[C:5]([CH3:19])([CH3:18])[CH2:6][C:7]1[NH:15][C:14]2[C:9](=[N:10][C:11]([O:16][CH3:17])=[CH:12][CH:13]=2)[CH:8]=1)[CH3:2].[Cl:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Cl)=[CH:24][CH:23]=1.C([O-])([O-])=O.[Cs+].[Cs+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C>[CH2:1]([O:3][C:4](=[O:20])[C:5]([CH3:19])([CH3:18])[CH2:6][C:7]1[N:15]([CH2:26][C:25]2[CH:28]=[CH:29][C:22]([Cl:21])=[CH:23][CH:24]=2)[C:14]2[C:9](=[N:10][C:11]([O:16][CH3:17])=[CH:12][CH:13]=2)[CH:8]=1)[CH3:2]

Participants

6

Reactant 3

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 10796Cesium carbonateHCID 59754778HCID 59754778, compound

Product 1

HCID 59754773HCID 59754773, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

3-(5-Methoxy-1H-pyrrolo[3,2-b]pyridin-2-yl)-2,2-dimethyl-propionic acid ethyl ester (0.350 g, 1.27 mmol), 4-chlorobenzyl chloride (0.306 g, 1.90 mmol), Cs2CO3 (0.825 g, 2.53 mmol), and tetrabutylammonium iodide (0.094 g, 0.25 mmol) were suspended in DMF (˜1 mL) and stirred at 60° C. overnight under N2. DMF was removed in vacuo, the residue was dissolved in ether and water, and the aqueous layer was extracted three times with ether. The combined organic layers were washed twice with water, once with brine, dried over MgSO4, filtered and concentrated. The crude material was purified by silica gel (0-100% EtOAc in hexanes) to obtain the desired ester.

Workup

  1. customDMF was removed in vacuo
  2. dissolutionthe residue was dissolved in ether
  3. extractionwater, and the aqueous layer was extracted three times with ether
  4. washThe combined organic layers were washed twice with water, once with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude material was purified by silica gel (0-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-3d795e27c3df422d86c53a77418bbb26
Source dataset
uspto-grants-2008_07
Patent number
US07405302B2

Reaction notes

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