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Trifluoroacetic acid → 2-(3-(1H-pyrazolo[3,4-b]pyridin-4-yl)phenyl)-2-methylbutanenitrile

HRID 384060
Notes
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Reaction equation

HRID 384060 reaction equation
[CH3:1][C:2]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]3[N:19](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:20]=[CH:21][C:14]=23)[CH:8]=1)([CH2:5][CH3:6])[C:3]#[N:4].C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[NH:19]1[C:15]2=[N:16][CH:17]=[CH:18][C:13]([C:9]3[CH:8]=[C:7]([C:2]([CH3:1])([CH2:5][CH3:6])[C:3]#[N:4])[CH:12]=[CH:11][CH:10]=3)=[C:14]2[CH:21]=[N:20]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 57969705HCID 57969705, compound

Product 1

HCID 579696382-(3-(1H-pyrazolo[3,4-b]pyridin-4-yl)phenyl)-2-methylbutanenitrileYield 72.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2-Methyl-2-(3-(1-trityl-1H-pyrazolo[3,4-b]pyridin-4-yl)phenyl)butanenitrile (240 mg, 0.46 mmol) was dissolved in dichloromethane (10 ml) and cooled down in an ice-bath. Triethylsilane (2.5 ml) was added followed by trifluoroacetic acid (2.5 ml). The resulting mixture was stirred at 0° C. for 2 hours and then concentrated under reduced pressure. The residue was partitioned between ethyl acetate and a saturated aqueous solution of sodium carbonate. The organic phase was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified on silica gel by flash column chromatography to afford the title compound as a white solid (92 mg, 70% yield).

Workup

  1. temperaturecooled down in an ice-bath
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was partitioned between ethyl acetate
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified on silica gel by flash column chromatography

Sources & evidence

ORD record
ord-e142016deaa94f85b170fec06d5ad514
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08367697B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes