HCID 178455209, compound → HCID 178455208, compound

HRID 1943876Notes

Reaction equation

HRID 1943876 reaction equation
[Si:1]([O:8][CH2:9][C:10]#[C:11][C:12]1[C:20]2[C:15](=[N:16][CH:17]=[C:18]([N+:21]([O-])=O)[CH:19]=2)[NH:14][N:13]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>C(OCC)(=O)C.CCO.[Pd]>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][C:12]1[C:20]2[C:15](=[N:16][CH:17]=[C:18]([NH2:21])[CH:19]=2)[NH:14][N:13]=1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 178455209HCID 178455209, compound

Product 1

HCID 178455208HCID 178455208, compoundYield 57.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

10% (wt.) Pd on activated carbon (0.017 g, 0.016 mmol) was added to a solution of 3-(3-(tert-butyldimethylsilyloxy)prop-1-ynyl)-5-nitro-1H-pyrazolo[3,4-b]pyridine (0.053 g, 0.160 mmol) in a mixture of ethyl acetate/EtOH (1:1, 6 mL). The reaction mixture was purged with nitrogen for 5 minutes and then stirred under a hydrogen balloon overnight. The reaction mixture was filtered through GF/F paper. The filter cake was rinsed with ethyl acetate, and the filtrate was concentrated. The crude product was purified by column chromatography, eluting with hexanes/ethyl acetate (2:1), hexanes/ethyl acetate (1:1) to give 3-(3-(tert-butyldimethylsilyloxy)propyl)-1H-pyrazolo[3,4-b]pyridin-5-amine (0.028 g, 57%) as an oil.

Workup

  1. customThe reaction mixture was purged with nitrogen for 5 minutes
  2. filtrationThe reaction mixture was filtered through GF/F paper
  3. washThe filter cake was rinsed with ethyl acetate
  4. concentrationthe filtrate was concentrated
  5. customThe crude product was purified by column chromatography
  6. washeluting with hexanes/ethyl acetate (2:1), hexanes/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-fccc9248336a4babb9750c7d5f299eb8
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

Loading…