Sodium hydride → HCID 59398559, compound

HRID 2070014Notes

Reaction equation

HRID 2070014 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.[H-].[Na+].[CH2:13]([O:20][CH2:21]Cl)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C=O)C>[CH2:13]([O:20][CH2:21][N:8]1[C:4]2=[N:5][CH:6]=[CH:7][C:2]([Cl:1])=[C:3]2[CH:10]=[CH:9]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 137983Benzyl chloromethyl etherHCID 113894934-Chloro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 59398559HCID 59398559, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Chloro-1H-pyrrolo[2,3-b]pyridine (20 g, 131 mmol) was dissolved in hydrous DMF (200 mL), and sodium hydride (60%, 6.0 g, 150 mmol) was added thereto. The resulting mixture was stirred under ice-cooling for 30 minutes, and then benzyloxymethyl chloride (26.8 g, 171 mmol) was added thereto. The resulting mixture was stirred under ice-cooling for 1 hour and then concentrated under reduced pressure. The residue was partitioned between ethyl acetate (300 mL) and saturated brine (200 mL). The aqueous layer was further extracted with ethyl acetate (300 mL). The combined organic layer was washed with saturated brine, dried, and concentrated. The residue was purified by silica-gel column chromatography (manufactured by Fuji Silysia, BW300 1500CC, n-hexane:EtOAc=4:1) to give 34 g of 1-benzyloxymethyl-4-chloro-1H-pyrrolo[2,3-b]pyridine as a light-yellow syrup (yield: 95%).

Workup

  1. temperaturecooling for 30 minutes
  2. stirringThe resulting mixture was stirred under ice-
  3. temperaturecooling for 1 hour
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was partitioned between ethyl acetate (300 mL) and saturated brine (200 mL)
  6. extractionThe aqueous layer was further extracted with ethyl acetate (300 mL)
  7. washThe combined organic layer was washed with saturated brine
  8. customdried
  9. concentrationconcentrated
  10. customThe residue was purified by silica-gel column chromatography (manufactured by Fuji Silysia, BW300 1500CC, n-hexane:EtOAc=4:1)

Sources & evidence

ORD record
ord-382f69fe2336446aa1d30309e1f466c9
Source dataset
uspto-grants-2012_10
Patent number
US08299252B2

Reaction notes

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