Water → HCID 58110670, compound

HRID 2096996Notes

Reaction equation

HRID 2096996 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][CH:9]=[CH:10][C:3]=12.[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[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:16][C:15]3[CH:18]=[CH:19][C:12]([F:11])=[CH:13][CH:14]=3)[CH:9]=[CH:10][C:3]=12

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 680214-Fluorobenzyl bromideHCID 113894934-Chloro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 58110670HCID 58110670, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 4-chloro-1H-pyrrolo[2,3-b]pyridine (300 mg, 2.00 mmol) in 5 ml DMF was added 4-Fluorobenzylbromide (0.27 ml, 2.2 mmol) then add NaH (80 mg, 2.0 mmol) and stir at room temperature overnight. Work up by adding water and EtOAc and 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 400 mg (77%) of product.

Workup

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

Sources & evidence

ORD record
ord-8cf7df4935434e4c864c7d7db00eeb29
Source dataset
uspto-grants-2013_05
Patent number
US08450343B2

Reaction notes

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