Sodium hydride → HCID 67078557, compound

HRID 1943860Notes

Reaction equation

HRID 1943860 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]2[CH:12]=[N:11][NH:10][C:7]2=[N:8][CH:9]=1.[CH3:13][Si:14]([CH3:21])([CH3:20])[CH2:15][CH2:16][O:17][CH2:18]Cl>C1COCC1.C(OCC)(=O)C>[Br:3][C:4]1[CH:5]=[C:6]2[CH:12]=[N:11][N:10]([CH2:18][O:17][CH2:16][CH2:15][Si:14]([CH3:21])([CH3:20])[CH3:13])[C:7]2=[N:8][CH:9]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 404274545-Bromopyrazolo[3,4-b]pyridine

Product 1

HCID 67078557HCID 67078557, compoundYield 152.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

NaH (0.082 g, 2.06 mmol, 60% suspension in mineral oil) was added portionwise to a cold (0° C.) solution of 5-bromo-1H-pyrazolo[3,4-b]pyridine (0.204 g, 1.03 mmol) in dry THF (10 mL). The reaction mixture was stirred at 0° C. for 10 minutes before 2-(trimethylsilyl)ethoxymethyl chloride (0.31 mL, 0.292 mmol) was added dropwise via a syringe. The reaction mixture was left at room temperature overnight. The reaction mixture was diluted with ethyl acetate (50 mL) and carefully quenched with water (10 mL). The aqueous layer was separated and extracted with ethyl acetate (3×50 mL). The combined organic layers were dried, filtered and concentrated. The crude product was purified by column chromatography, eluting with hexanes/ethyl acetate (50:1) to give 5-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-b]pyridine (0.146 g, 43%) as an oil.

Workup

  1. additionwas added dropwise via a syringe
  2. customcarefully quenched with water (10 mL)
  3. customThe aqueous layer was separated
  4. extractionextracted with ethyl acetate (3×50 mL)
  5. customThe combined organic layers were dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by column chromatography
  9. washeluting with hexanes/ethyl acetate (50:1)

Sources & evidence

ORD record
ord-2ee2da377b004064ab87c9b1d5e7e961
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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