Water → 4-chloro-1-(4-fluorobenzyl)-1H-pyrrolo[3,2-c]pyridine

HRID 2097000Notes

Reaction equation

HRID 2097000 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[F:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16]Br)=[CH:14][CH:13]=1.[H-].[Na+].O>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[C:3]2[CH:4]=[CH:5][N:6]([CH2:16][C:15]3[CH:18]=[CH:19][C:12]([F:11])=[CH:13][CH:14]=3)[C:7]=2[CH:8]=[CH:9][N:10]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 680214-Fluorobenzyl bromideHCID 141143844-chloro-1H-pyrrolo[3,2-c]pyridine

Product 1

HCID 581106824-chloro-1-(4-fluorobenzyl)-1H-pyrrolo[3,2-c]pyridineYield 50%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 4-Chloro-5-azaindole (120 mg, 079 mmol) in 5 ml DMF was added 4-Fluorobenzylbromide (0.120 ml, 0.95 mmol) then add NaH (32 mg, 0.79 mmol) and stir at room temperature overnight. Work up reaction by adding water and EtOAc then extract three times with EtOAc. Pool all organics and wash one time with brine then dry over sodium sulfate, filter and concentrate to dryness. The residue was purified by chromatography over silica gel (eluted with Hexanes/EtOAc 99:1 to 50:50) to provide 100 mg (50%) of product.

Workup

  1. customreaction
  2. extractionthen extract three times with EtOAc
  3. washPool all organics and wash one time with brine
  4. dry with materialthen dry over sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate to dryness
  7. customThe residue was purified by chromatography over silica gel (eluted with Hexanes/EtOAc 99:1 to 50:50)

Sources & evidence

ORD record
ord-acb0aef437ee4f06bedbd51e0c281ede
Source dataset
uspto-grants-2013_05
Patent number
US08450343B2

Reaction notes

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