2-Chloromethyl 2-(trimethylsilyl)ethyl ether → HCID 59763216, compound

HRID 218465Notes

Reaction equation

HRID 218465 reaction equation
CC([O-])(C)C.[K+].[NH:7]1[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[N:8]1.[CH3:16][Si:17]([CH2:20][CH2:21][O:22][CH2:23]Cl)([CH3:19])[CH3:18]>C1COCC1.CCOC(C)=O.O>[CH3:16][Si:17]([CH3:19])([CH3:18])[CH2:20][CH2:21][O:22][CH2:23][N:7]1[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[N:8]1

Participants

7

Reactant 3

HCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 216436531H-Pyrazolo(4,3-b)pyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 59763216HCID 59763216, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

KOtBu (2.38 g, 21.24 mmol) was added to a solution of 1H-pyrazolo[4,3-b]pyridine (2.3 g, 19.3 mmol) in THF (60 mL) at 0° C. After stirring at 0° C. for 1 hr, trimethylsilylethoxymethyl chloride (3.54 g, 21.24 mmol) was added. The reaction mixture was kept at 0° C. for 1 hr with stirring, then 1.5 hr at rt. The mixture was diluted with EtOAc and water and extracted with EtOAc. The combined organic phases were washed with brine, dried with Na2SO4, and concentrated. The crude product was purified by flash chromatography to afford 1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-pyrazolo[4,3-b]pyridine in (2.32 g, 48%) and the regio-isomer.

Workup

  1. waitThe reaction mixture was kept at 0° C. for 1 hr
  2. stirringwith stirring
  3. custom1.5 hr
  4. customat rt
  5. extractionextracted with EtOAc
  6. washThe combined organic phases were washed with brine
  7. dry with materialdried with Na2SO4
  8. concentrationconcentrated
  9. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-dc310f0f6062423088ee6ba48e2bf510
Source dataset
uspto-grants-2012_06
Patent number
US08198456B2

Reaction notes

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