Trifluoroacetic acid → HCID 57963161, compound

HRID 1403252Notes

Reaction equation

HRID 1403252 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:9])=[N:6][C:7]=1[CH3:8].[CH3:10][O:11][C:12]1[N:17]=[CH:16][C:15]([CH:18]=O)=[CH:14][CH:13]=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>C(#N)C>[I:1][C:2]1[CH:3]=[CH:4][C:5]([NH:9][CH2:18][C:15]2[CH:16]=[N:17][C:12]([O:11][CH3:10])=[CH:13][CH:14]=2)=[N:6][C:7]=1[CH3:8]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 9596135-Iodo-6-methylpyridin-2-amineHCID 33645766-Methoxypyridine-3-carbaldehyde

Product 1

HCID 57963161HCID 57963161, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-Iodo-6-methyl-pyridin-2-ylamine (28, 1.7 g, 7.3 mmol) and 6-methoxy-pyridine-3-carbaldehyde (29, 1.1 g, 8.0 mmol) were combined in a round bottom flask with trifluoroacetic acid (2.80 mL, 36.3 mmol), triethylsilane (5.80 mL, 36.3 mmol) and 50 mL of acetonitrile. The reaction was stirred at room temperature overnight, then heated to reflux for 6 hours. The reaction was concentrated under vacuum, combined with aqueous potassium carbonate and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel flash column chromatography, eluting with 10-100% ethyl acetate in hexane. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound (30, 1.80 g). MS (ESI)[M+H+]+=356.80.

Workup

  1. temperatureheated
  2. temperatureto reflux for 6 hours
  3. concentrationThe reaction was concentrated under vacuum
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated under vacuum
  8. customThe resulting material was purified by silica gel flash column chromatography
  9. washeluting with 10-100% ethyl acetate in hexane
  10. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-1c95c294af7f4d1096f8fd87e9910fd1
Source dataset
uspto-grants-2014_12
Patent number
US08912204B2

Reaction notes

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