Trifluoroacetic acid → 3-[(3-Nitrophenyl)methyl]-5-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine

HRID 1261067Notes

Reaction equation

HRID 1261067 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10](OC)[C:11]2[C:19]3[C:14](=[N:15][CH:16]=[C:17]([C:20]4[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=4)[CH:18]=3)[NH:13][CH:12]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].FC(F)(F)C(O)=O.C([SiH](CC)CC)C.C(=O)(O)[O-].[Na+]>C(#N)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][CH:9]=1)[CH2:10][C:11]1[C:19]2[C:14](=[N:15][CH:16]=[C:17]([C:20]3[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=3)[CH:18]=2)[NH:13][CH:12]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 58087339HCID 58087339, compound

Product 1

HCID 580876073-[(3-Nitrophenyl)methyl]-5-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 3-[(3-nitro-phenyl)-methoxy-methyl]-5-pyridin-3-yl-1H-pyrrolo[2,3-b]pyridine (535, 431 mg, 1.20 mmol, per Example 26, Scheme 49 Step 1) in acetonitrile (130 mL), were added trifluoroacetic acid (18 mL, 230 mmol) and triethylsilane (36 mL, 230 mmol). The reaction was refluxed for three hours. The reaction mixture was poured into sodium bicarbonate solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 80% ethyl acetate in hexane to give the compound (P-1402, 323 mg, 82%). MS (ESI) [M+H+]+=331.2.

Workup

  1. temperatureThe reaction was refluxed for three hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. custompurified by silica gel column chromatography
  8. washeluting with 80% ethyl acetate in hexane
  9. customto give the compound (P-1402, 323 mg, 82%)

Sources & evidence

ORD record
ord-b33af966afbe4762ab7f22dff2a67dce
Source dataset
uspto-grants-2013_06
Patent number
US08470818B2

Reaction notes

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