Dimethylformamide → HCID 59327230, compound

HRID 410293Notes

Reaction equation

HRID 410293 reaction equation
[F:1][C:2]1[C:7](I)=[CH:6][CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C.[O:20]1[CH2:24][CH:23]=[CH:22][CH2:21]1>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[O:20]1[CH:21]=[CH:22][CH:23]([C:7]2[C:2]([F:1])=[N:3][CH:4]=[CH:5][CH:6]=2)[CH2:24]1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 155702,5-DihydrofuranHCID 70095012-Fluoro-3-iodopyridine

Product 1

HCID 59327230HCID 59327230, compound

Reagents, catalysts & solvents 3

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

To a 500 mL round bottomed flask charged with 2-fluoro-3-iodopyridine (15.05 g, 67.5 mmol, Asymchem), tetrabutylammonium chloride (18.80 g, 67.6 mmol, Alfa Aesar), potassium carbonate (28.60 g, 207 mmol, Aldrich) and palladium(ii) acetate (1.48 g, 6.59 mmol, Strem) was added DMF (75 mL) followed by 2,5-dihydrofuran (50.00 mL, 678 mmol, Aldrich) and the reaction mixture was stirred vigorously at 25° C. for 2 h. The mixture was poured into 500 mL of water and the mixture was extracted with EtOAc (3×). The combined organic layers were evaporated onto silica gel and purified by flash chromatography (Isco (330 gram)) eluting with EtOAc:hexanes (0:1→1:2) to give a clear colorless oil. MS (ESI, pos. ion) m/z: 166.1 (M+1).

Workup

  1. extractionthe mixture was extracted with EtOAc (3×)
  2. customThe combined organic layers were evaporated onto silica gel
  3. custompurified by flash chromatography (Isco (330 gram))
  4. washeluting with EtOAc:hexanes (0:1→1:2)
  5. customto give a clear colorless oil

Sources & evidence

ORD record
ord-18de076402d74d1fbe5ad21cded46731
Source dataset
uspto-grants-2014_06
Patent number
US08759532B2

Reaction notes

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