Sodium hydride → HCID 68672308, compound

HRID 1927652Notes

Reaction equation

HRID 1927652 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[N:2]1.[H-].[Na+].[CH3:12][Si:13]([CH2:16][CH2:17][O:18][CH2:19]Cl)([CH3:15])[CH3:14]>CN(C=O)C>[CH3:12][Si:13]([CH3:15])([CH3:14])[CH2:16][CH2:17][O:18][CH2:19][N:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[N:2]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 27558501H-pyrazolo(3,4-b)pyridine

Product 1

HCID 68672308HCID 68672308, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1H-pyrazolo[3,4-b]pyridine (380 mg, 3.2 mmol) in DMF (5 mL) was added NaH (60% dispersion in mineral oil, 153 mg, 3.8 mmol). After stirring for 20 min, the mixture was heated with a heat gun and then allowed to cool to rt. SEM-Cl (647 μL, 3.8 mmol) was added dropwise and stirring continued for 2 h. The resulting mixture was partitioned between water and ethyl acetate. The organic layer was separated and concentrated, and the residue was purified by flash column chromatography (silica gel, eluting with 0-50% ethyl acetate in hexanes) to provide 1-(2-trimethylsilanylethoxymethyl)-1H-pyrazolo[3,4-b]pyridine, which was dissolved in ethanol (30 mL) and flushed with a nitrogen stream. Palladium on charcoal (5% wet on carbon, ˜50 mg) was added and the mixture was placed under hydrogen (50 psi) for 2 days. The reaction mixture was filtered, and the filtrate was concentrated to provide the title compound: 1H NMR (500 MHz, CDCl3) δ 7.13 (s, 1H), 5.24 (s, 2H), 3.68 (br, 1H), 3.54 (t, J=8.2 Hz, 2H), 3.28 (m, 2H), 2.51 (t, J=6.1, 2H), 1.81 (m, 2H), 0.89 (t, J=8.2 Hz, 2H), −0.01 (s, 9H).

Workup

  1. temperaturethe mixture was heated with a heat gun
  2. stirringstirring
  3. waitcontinued for 2 h
  4. customThe resulting mixture was partitioned between water and ethyl acetate
  5. customThe organic layer was separated
  6. concentrationconcentrated
  7. customthe residue was purified by flash column chromatography (silica gel, eluting with 0-50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-15105c6e5f164b4989a5b7a3def8c41a
Source dataset
uspto-grants-2012_05
Patent number
US08183275B2

Reaction notes

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