Sodium hydride → 4-Chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo(2,3-b)pyridine

HRID 1851090Notes

Reaction equation

HRID 1851090 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+].[CH3:13][Si:14]([CH2:17][CH2:18][O:19][CH2:20]Cl)([CH3:16])[CH3:15]>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:20][O:19][CH2:18][CH2:17][Si:14]([CH3:16])([CH3:15])[CH3:13])[CH:9]=[CH:10][C:3]=12

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 113894934-Chloro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 116735894-Chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo(2,3-b)pyridineYield 74.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

4-Chloro-1H-pyrrolo[2,3-b]pyridine (170 mg, 1.114 mmol) was dissolved in tetrahydrofuran (2 mL) under nitrogen atmosphere. After cooling to 0° C., 40% NaH (30 mg, 1.224 mmol) was added. The resulting reaction mixture was stirred for 15 minutes and then heated at 80° C. for 3 hours after adding SEM-Cl (185 mg, 1.114 mmol). The heated reaction mixture was cooled to room temperature and then extracted with dichloromethane and water. The organic layer was separated and washed with sodium chloride aqueous solution. The organic layer was dried with magnesium sulfate and then filtered. The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (ethyl acetate:hexane=1:1) to give the target compound as a yellow oil (235 mg, 0.83 mmol, 74% yield).

Workup

  1. customThe resulting reaction mixture
  2. temperatureheated at 80° C. for 3 hours
  3. customThe heated reaction mixture
  4. temperaturewas cooled to room temperature
  5. extractionextracted with dichloromethane and water
  6. customThe organic layer was separated
  7. washwashed with sodium chloride aqueous solution
  8. dry with materialThe organic layer was dried with magnesium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated under reduced pressure
  11. customThe resulting residue was purified by silica gel chromatography (ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-516958f9b8e5463dafed8a923ef59d76
Source dataset
uspto-grants-2015_02
Patent number
US08957102B2

Reaction notes

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