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

HRID 44670Notes

Reaction equation

HRID 44670 reaction equation
C([N:20]1[C:24]2=[N:25][CH:26]=[CH:27][C:28]([C:29]3[S:30][CH:31]=[C:32]([CH2:34][C:35]#[N:36])[N:33]=3)=[C:23]2[CH:22]=[N:21]1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:20]1[C:24]2=[N:25][CH:26]=[CH:27][C:28]([C:29]3[S:30][CH:31]=[C:32]([CH2:34][C:35]#[N:36])[N:33]=3)=[C:23]2[CH:22]=[N:21]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 666434512-[2-(1-Tritylpyrazolo[5,4-b]pyridin-4-yl)thiazol-4-yl]acetonitrile

Product 1

HCID 498048042-(2-(1H-pyrazolo[3,4-b]pyridin-4-yl)thiazol-4-yl)ethanenitrileYield 16%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-[2-(1-tritylpyrazolo[5,4-b]pyridin-4-yl)thiazol-4-yl]acetonitrile (83 mg, 0.1716 mmol) in DCM (3 ml) was treated with triethylsilane (0.5 ml) followed by TFA (0.5 mL). After 15 minutes the mixture was concentrated in vacuo and purified by column chromatography (70:9:1 DCM/MeOH/NH4OH) to give the product as a light tan solid (6.5 mg, 16% Yield). 1H NMR (DMSO, 400 MHz) δ 4.37 (2H, s), 7.72 (1H, d), 7.94 (1H, s), 8.63 (1H, s), 8.66 (1H, d), 13.98 (1H, br s); MS (ES+) 242.00

Workup

  1. concentrationAfter 15 minutes the mixture was concentrated in vacuo
  2. custompurified by column chromatography (70:9:1 DCM/MeOH/NH4OH)

Sources & evidence

ORD record
ord-049e89e742c14aa483f0a1ba63590630
Source dataset
uspto-grants-2013_09
Patent number
US08541445B2

Reaction notes

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