1-Chloro-4-(chloromethyl)benzene → HCID 59754791, compound

HRID 1713415Notes

Reaction equation

HRID 1713415 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[CH:11]=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[NH:9][C:6]2=[N:7][CH:8]=1.[H-].[Na+].[Cl:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Cl)=[CH:22][CH:21]=1>CN(C=O)C.C1COCC1>[Cl:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][N:9]2[C:6]3=[N:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=[C:5]3[CH:11]=[C:10]2[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 24758Sodium hydrideHCID 59754779HCID 59754779, compound

Product 1

HCID 59754791HCID 59754791, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To Ethyl 5-methoxy-1H-pyrrolo[2,3-b]pyridine-2-carboxylate isolated in step 3 (166 mg; 0.753 mmol) in DMF (2 mL) and THF (1 mL) cooled to 0° C. was added solid sodium hydride (60% dispersion in mineral oil; 40 mg, 1.00 mmol) and the solution allowed to warm to ambient temperature. 4-chlorobenzylchloride (181 mg, 1.12 mmol) was then added and the reaction maintained at ambient temperature. After completion (as determined by TLC analysis) the reaction mixture was partitioned between EtOAc and water, the aqueous layer extracted with EtOAc, the combined organic phases dried (MgSO4), filtered and evaporated. The residue was purified on silica gel eluting with a gradient of 0 to 10% EtOAc in hexanes to afford the title compound as a colorless solid.

Workup

  1. temperaturethe reaction maintained at ambient temperature
  2. customAfter completion (as determined by TLC analysis) the reaction mixture was partitioned between EtOAc and water
  3. extractionthe aqueous layer extracted with EtOAc
  4. dry with materialthe combined organic phases dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified on silica gel eluting with a gradient of 0 to 10% EtOAc in hexanes

Sources & evidence

ORD record
ord-48fd98e3954a450bb843f498a9a1dbc0
Source dataset
uspto-grants-2010_09
Patent number
US07795274B2

Reaction notes

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