Potassium Carbonate → HCID 10332109, compound

HRID 2222270Notes

Reaction equation

HRID 2222270 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=2)=[CH:2]1.F[C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[C:16]#[N:17].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[N:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[C:3]1[CH:4]=[CH:5][N:1]([C:13]2[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=2)[C:16]#[N:17])[CH:2]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 678803-FluorobenzonitrileHCID 8203972-(1H-pyrrol-3-yl)Pyridine

Product 1

HCID 10332109HCID 10332109, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(1H-Pyrrol-3-yl)pyridine (0.144 g, 11.0 mmol), 3-fluorobenzonitrile (1.21 g, 10 mmol), and potassium carbonate (0.0.276 g, 2 mmol) were heated at 145° C. in DMF (0.5 mL) for 14 h. After this time, the reaction mixture was cooled to rt and quenched with H2O (30 mL). The mixture was extracted with EtOAc (3×25 mL) and the combined organic extracts washed with brine. The organic phase was dried over Na2SO4, concentrated in vacuo and the residue was chromatographed on silica gel eluting with EtOAc:hexane (2:3) to afford a white solid which was recrystallized from dichloromethane-hexane to give 3-(3-pyridin-2-yl-1H-pyrrol-1-yl)benzonitrile as white crystals. 1H NMR (CD3Cl, 300 MHz) δ 8.59 (ddd, 1H), 7.78˜7.71 (m, 3H), 7.68 (dd, 1H), 7.62˜7.53 (m, 3H), 7.17˜7.11 (m, 2H), 6.89 (dd, 1H). MS (ES) 246.1 (M++H).

Workup

  1. customquenched with H2O (30 mL)
  2. extractionThe mixture was extracted with EtOAc (3×25 mL)
  3. washthe combined organic extracts washed with brine
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customthe residue was chromatographed on silica gel eluting with EtOAc:hexane (2:3)
  7. customto afford a white solid which
  8. customwas recrystallized from dichloromethane-hexane

Sources & evidence

ORD record
ord-5a0630e385d44ed0a2b236525565002e
Source dataset
uspto-grants-2008_05
Patent number
US07371767B2

Reaction notes

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