6-Chloro-3-pyridinecarbonitrile → HCID 11140234, compound

HRID 853807Notes

Reaction equation

HRID 853807 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1.C([Sn](CCCC)(CCCC)[C:15]1[O:16][C:17]([Sn](CCCC)(CCCC)CCCC)=[CH:18][CH:19]=1)CCC>O1CCOCC1>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([C:17]2[O:16][C:15]([C:2]3[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=3)=[CH:19][CH:18]=2)=[N:3][CH:4]=1)#[N:7]

Participants

4

Reactant 2

HCID 51520946-Chloro-3-pyridinecarbonitrileHCID 115782772,5-Bis(tri-n-butylstannyl)furan

Product 1

HCID 11140234HCID 11140234, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Referring now to Scheme 4, a mixture of 6-chloronicotinonitrile (1.38 g, 10 mmol), 2,5-bis(tri-n-butylstannyl)furan (3.2 g, 5 mmol) and tetrakis(triphenyl-phosphine)palladium(0) (125 mg) in dry 1,4-dioxane (40 mL) was heated under nitrogen at reflux (100–110° C.) for 24 h. The solvent was evaporated under reduced pressure and the residue was dissolved in methylene chloride and the solution was passed through CELITE® matrix (available from Word Minerals Corporation of Santa Barbara, Calif., United States of America) to remove Pd. The solution was evaporated, filtered and the precipitate was washed with hexanes to afford 21 in 85% yield, mp 311–312° C. (DMF). 1H nmr (DMSO-d6); δ 7.55 (s, 2H), 8.20 (d, J=8.4 Hz, 2H), 8.44 (dd, J=8.4, 2.1 Hz, 2H). 9.06 (d, J=2.1 Hz, 2H). 13C nmr; δ 153.5, 152.8, 150.0, 141.0, 118.8, 117.1, 114.8, 107.3. Calcd. for C16H8N4O: C, 70.58; H, 2.96; N, 20.57. Found. C, 70.35; H, 3.04; N, 20.35.

Workup

  1. temperaturewas heated under nitrogen
  2. temperatureat reflux (100–110° C.) for 24 h
  3. customThe solvent was evaporated under reduced pressure
  4. dissolutionthe residue was dissolved in methylene chloride
  5. customto remove Pd
  6. customThe solution was evaporated
  7. filtrationfiltered
  8. washthe precipitate was washed with hexanes

Sources & evidence

ORD record
ord-da49dfc27dfc47bf81b074d09dc0a79a
Source dataset
uspto-grants-2007_08
Patent number
US07256203B2

Reaction notes

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