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Pyridine → (E)-Ethyl 3-[6-[[3,5-bis(trimethylsilyl)benzoyl]amino]pyridin-3-yl]acrylate

HRID 2265083
Notes
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Reaction equation

HRID 2265083 reaction equation
[CH3:1][Si:2]([CH3:17])([CH3:16])[C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([Si:12]([CH3:15])([CH3:14])[CH3:13])[CH:11]=1)[C:6]([OH:8])=O.N1C=CC=CC=1.[NH2:24][C:25]1[N:30]=[CH:29][C:28]([CH:31]=[CH:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:27][CH:26]=1.P(Cl)(Cl)(Cl)=O>C(#N)C.C(OCC)(=O)C.O>[CH3:16][Si:2]([CH3:1])([CH3:17])[C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([Si:12]([CH3:15])([CH3:14])[CH3:13])[CH:11]=1)[C:6]([NH:24][C:25]1[N:30]=[CH:29][C:28](/[CH:31]=[CH:32]/[C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:27][CH:26]=1)=[O:8]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 1049PyridineHCID 24813Phosphorus oxychlorideHCID 146056473,5-Bis(trimethylsilyl)benzoic acid2×HCID 53409341Ethyl 3-(6-aminopyridine-3-yl)acrylate

Product 1

HCID 86644273(E)-Ethyl 3-[6-[[3,5-bis(trimethylsilyl)benzoyl]amino]pyridin-3-yl]acrylateYield 20%

Reagents, catalysts & solvents

3
HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

3,5-Bis(trimethylsilyl)benzoic acid (hereinafter referred to as “BTMB”; 700 mg) was suspended in acetonitrile (5.25 ml) in a nitrogen atmosphere. Pyridine (0.212 ml) and Compound 1a (603 mg) were added to the suspension, and phosphorus oxychloride (0.131 ml) was added dropwise under ice-cooling. The mixture was stirred while refluxing under heating for 3.5 hours. After the reaction mixture was allowed to cool, water and ethyl acetate were added thereto. The organic layer was washed three times with water and once with a saturated sodium chloride solution, and then dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by neutral silica gel column chromatography (5% ethyl acetate/n-hexane) to obtain Compound 1b (232 mg, 20%) as a white foam.

Workup

  1. additionwas added dropwise under ice-
  2. temperaturecooling
  3. temperaturewhile refluxing
  4. temperatureunder heating for 3.5 hours
  5. temperatureto cool
  6. washThe organic layer was washed three times with water
  7. dry with materialonce with a saturated sodium chloride solution, and then dried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off
  9. customthe residue was purified by neutral silica gel column chromatography (5% ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-cf62d2e8f9544323a2b440b5956b3cc9
Source dataset
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07855300B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes