2,6-Dichloropyridine → HCID 10236225, compound

HRID 746836Notes

Reaction equation

HRID 746836 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.[H-].[Na+].[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17](Cl)[N:16]=1>CN(C=O)C>[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N:1]2[CH:5]=[CH:4][C:3]([C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=3)=[CH:2]2)[N:16]=1

Participants

5

Reactant 3

HCID 169892,6-DichloropyridineHCID 24758Sodium hydrideHCID 8203972-(1H-pyrrol-3-yl)Pyridine

Product 1

HCID 10236225HCID 10236225, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 2-(1H-pyrrol-3-yl)pyridine (432 mg, 3.0 mmol) in DMF (15 mL) at 50° C. was added NaH (3.15 mmol, 60% suspension in oil). After 10 min, 2,6-dichloropyridine (1.33 g, 9.0 mmol) was added, and the reaction was warmed to 120° C., stirred for 18 h, then quenched with water (100 mL) and partitioned with EtOAc (100 mL). The aqueous layer was washed with additional EtOAc (2×75 mL). The combined organic extracts were dried over MgSO4, filtered, and concentrated in vacuo. The crude residue was purified by liquid chromatography on SiO2 eluting with 1:1 hexanes:EtOAc to afford 2-chloro-6-(3-pyridin-2-yl-1H-pyrrol-1-yl)pyridine as a tan solid. H-NMR (CDCl3, 500 MHz) δ 8.60 (d, 1H), 8.13 (dd, 1H), 7.66-7.79 (m, 2H), 7.57-7.61 (m, 2H), 7.31 (d, 1H), 7.16 (d, 1H), 7.11 (dd, 1H), 6.88 (m, 1H).

Workup

  1. customquenched with water (100 mL)
  2. custompartitioned with EtOAc (100 mL)
  3. washThe aqueous layer was washed with additional EtOAc (2×75 mL)
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by liquid chromatography on SiO2 eluting with 1:1 hexanes

Sources & evidence

ORD record
ord-7b060e62ee7f4fd49854e9da2d2a2851
Source dataset
uspto-grants-2008_07
Patent number
US07393959B2

Reaction notes

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