Tetrahydrofuran → HCID 178455209, compound

HRID 1943875Notes

Reaction equation

HRID 1943875 reaction equation
Br[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=2)[N:4](S(C2C=CC(C)=CC=2)(=O)=O)[N:3]=1.[C:24]([Si:28]([CH3:34])([CH3:33])[O:29][CH2:30][C:31]#[CH:32])([CH3:27])([CH3:26])[CH3:25].C1COCC1>[Cu]I.C(N(CC)CC)C>[Si:28]([O:29][CH2:30][C:31]#[C:32][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=2)[NH:4][N:3]=1)([C:24]([CH3:25])([CH3:26])[CH3:27])([CH3:33])[CH3:34]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 3445622tert-Butyl(dimethyl)[(prop-2-yn-1-yl)oxy]silaneHCID 67088990HCID 67088990, compound

Product 1

HCID 178455209HCID 178455209, compoundYield 17.1%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8471TriethylamineSolvent

Procedure

Triethylamine (4 mL) was added to a solution of 3-bromo-5-nitro-1-tosyl-1H-pyrazolo[3,4-b]pyridine (0.825 g, 3.40 mmol), tert-butyldimethyl(prop-2-ynyloxy)silane (0.89 g, 5.09 mmol) in THF (20 mL) PdCl2(PPh3)2 (0.119 g, 0.170 mmol) was added to the mixture, and the mixture was stirred at room temperature for 5 minutes before CuI (0.065 g, 0.34 mmol) was added. The reaction mixture was heated to reflux under argon for 40 hours. The reaction mixture was cooled to room temperature and concentrated. The crude product was purified by column chromatography, eluting with hexanes/ethyl acetate (4:1) to give 3-(3-(tert-butyldimethylsilyloxy)prop-1-ynyl)-5-nitro-1H-pyrazolo[3,4-b]pyridine (0.193 g, 17%) as a solid.

Workup

  1. additionwas added to the mixture
  2. additionwas added
  3. temperatureThe reaction mixture was heated
  4. temperatureto reflux under argon for 40 hours
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography
  7. washeluting with hexanes/ethyl acetate (4:1)

Sources & evidence

ORD record
ord-2c5215583ccc439db45ca8bbe59d1abf
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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