Benzyl Bromide → HCID 59490887, compound

HRID 1952222Notes

Reaction equation

HRID 1952222 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:14][C:13]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[C:7]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[F:21])=[O:5])[CH3:2].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[H-].[Na+].[C:32](OCC)(=O)C>CN(C=O)C.O>[CH2:1]([O:3][C:4]([C:6]1[N:14]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:13]2[C:8](=[N:9][C:10]([CH3:32])=[CH:11][CH:12]=2)[C:7]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[F:21])=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 59490941HCID 59490941, compound

Product 1

HCID 59490887HCID 59490887, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3-(2-Fluoro-phenyl)-1H-pyrrolo[3,2-b]pyridine-2-carboxylic acid ethyl ester A5 (0.02 g, 0.07 mmol) was diluted with DMF (1 mL). To the resulting solution was added benzyl bromide (0.1 mmol) and sodium hydride (0.077 mmol). The resulting suspension was stirred at room temperature for 14 hours, then ethyl acetate (50 mL) and water (20 mL) were added to the reaction mixture and layers were separated. The organic layer was sequentially washed with aqueous saturated sodium bicarbonate solution (10 mL), water (10 mL) and saturated brine (10 mL). The separated organic solution was dried (magnesium sulfate), filtered and concentrated in vacuo to provide a crude residue which was purified using flash chromatography to provide 1-Benzyl-3-(2-fluoro-phenyl)-5-methyl-1H-pyrrolo[3,2-b]pyridine-2-carboxylic acid ethyl ester A6 (94% yield). MS: 389.2 (M+H)+.

Workup

  1. customwere separated
  2. washThe organic layer was sequentially washed with aqueous saturated sodium bicarbonate solution (10 mL), water (10 mL) and saturated brine (10 mL)
  3. dry with materialThe separated organic solution was dried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto provide a crude residue which
  7. customwas purified

Sources & evidence

ORD record
ord-3e407134a78646c6b97a4c05b909f79e
Source dataset
uspto-grants-2013_03
Patent number
US08404845B2

Reaction notes

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