Trifluoroacetic acid → HCID 57619253, compound

HRID 1024305Notes

Reaction equation

HRID 1024305 reaction equation
[F:1][C:2]([F:40])([F:39])[C:3]1[CH:38]=[CH:37][C:6]([CH2:7][NH:8][C:9]2[N:14]=[CH:13][C:12]([C:15]([C:18]3[C:26]4[C:21](=[N:22][CH:23]=[CH:24][CH:25]=4)[N:20]([Si](C(C)C)(C(C)C)C(C)C)[CH:19]=3)(O)[CH3:16])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>C(#N)C>[NH:20]1[C:21]2=[N:22][CH:23]=[CH:24][CH:25]=[C:26]2[C:18]([C:15]([C:12]2[CH:11]=[CH:10][C:9]([NH:8][CH2:7][C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:40])[F:39])=[CH:38][CH:37]=3)=[N:14][CH:13]=2)=[CH2:16])=[CH:19]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 66970896HCID 66970896, compound

Product 1

HCID 57619253HCID 57619253, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-[6-(4-Trifluoromethyl-benzylamino)-pyridin-3-yl]-1-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-ethanol (622, 125.0 mg, 0.22 mmol) was dissolved in acetonitrile (11.7 mL) and trifluoroacetic acid (0.175 mL, 2.3 mmol) and triethylsilane (0.292 mL, 1.8 mmol) were added. The reaction was heated to reflux overnight. The reaction was concentrated, then washed with ethyl acetate and saturated sodium bicarbonate. The organic portions were dried with anhydrous sodium sulfate, filtered and the filtrate was adsorbed onto silica. The mixture was purified by silica gel chromatography (0-60% ethyl acetate:hexanes) to provide the desired compound (623, 43 mg, 50%), consistent with the compound structure by 1H-NMR.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux overnight
  3. concentrationThe reaction was concentrated
  4. washwashed with ethyl acetate and saturated sodium bicarbonate
  5. dry with materialThe organic portions were dried with anhydrous sodium sulfate
  6. filtrationfiltered
  7. customThe mixture was purified by silica gel chromatography (0-60% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-538199c67c124a5385ad353e191560bb
Source dataset
uspto-grants-2014_05
Patent number
US08722702B2

Reaction notes

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