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

HRID 44671Notes

Reaction equation

HRID 44671 reaction equation
[CH3:1][C:2]([C:6]1[N:7]=[C:8]([C:11]2[CH:16]=[CH:15][N:14]=[C:13]3[N:17](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:18]=[CH:19][C:12]=23)[S:9][CH:10]=1)([CH3:5])[C:3]#[N:4].C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:17]1[C:13]2=[N:14][CH:15]=[CH:16][C:11]([C:8]3[S:9][CH:10]=[C:6]([C:2]([CH3:5])([CH3:1])[C:3]#[N:4])[N:7]=3)=[C:12]2[CH:19]=[N:18]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 666435592-Methyl-2-[2-(1-tritylpyrazolo[5,4-b]pyridin-4-yl)thiazol-4-yl]propanenitrile

Product 1

HCID 666456192-(2-(1H-pyrazolo[3,4-b]pyridin-4-yl)thiazol-4-yl)-2-methyl propanenitrileYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-methyl-2-[2-(1-tritylpyrazolo[5,4-b]pyridin-4-yl)thiazol-4-yl]propanenitrile (239 mg, 0.4671 mmol) in DCM (6 mL) was treated with triethylsilane (727.8 mg, 999.7 μL, 6.259 mmol) followed by dropwise addition of TFA (296.0 mg, 200.0 μL, 2.596 mmol). The mixture was allowed to stir for 1 hour and then concentrated in vacuo and purified by column chromatography (EtOAc) to give the desired product as a yellow solid (97.5 mg, 78% Yield). 1H NMR (DMSO, 400 MHz) δ 1.84 (6H, s), 7.73 (1H, d), 8.04 (1H, s), 8.64 (1H, s), 8.67 (1H, d), 13.98 (1H, br s); MS (ES+) 270.03

Workup

  1. concentrationconcentrated in vacuo
  2. custompurified by column chromatography (EtOAc)

Sources & evidence

ORD record
ord-ff23ababa25144aa9e6b441e09a4f2e8
Source dataset
uspto-grants-2013_09
Patent number
US08541445B2

Reaction notes

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