Water → 5-(2-Thienyl)-2-dimethylaminopyridine

HRID 1837953Notes

Reaction equation

HRID 1837953 reaction equation
[Mg].Br[C:3]1[S:4][CH:5]=[CH:6][CH:7]=1.Br[C:9]1[CH:10]=[CH:11][C:12]([N:15]([CH3:17])[CH3:16])=[N:13][CH:14]=1.O>C1COCC1>[S:4]1[CH:5]=[CH:6][CH:7]=[C:3]1[C:9]1[CH:10]=[CH:11][C:12]([N:15]([CH3:17])[CH3:16])=[N:13][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 138512-Bromothiophene2×HCID 38030415-bromo-N,N-dimethylpyridin-2-amineHCID 5462224Magnesium

Product 1

HCID 226776615-(2-Thienyl)-2-dimethylaminopyridineYield 29.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of magnesium (0.119 g, 4.97 mmol) in THF (3 mL) was added 2-bromothiophene (0.811 g, 4.97 mmol) and the reaction mixture was stirred for 3 h. Another equivalent of 2-bromothiophene (0.811 g, 4.97 mmol) was added and the reaction mixture was heated at the reflux temperature for 2 h, then allowed to cool to room temperature. The resulting mixture was added to a solution of 5-bromo-2-dimethylaminopyridine (1.0 g, 4.97 mmol) in THF (12 mL) and the reaction was heated at the reflux temperature for 11 h, then was allowed to cool to room temperature. The resulting mixture was treated with water (10 mL), extracted with EtOAc (3×30 mL), dried (MgSO4) and concentrated under reduced pressure. The crude product was purified by flash chromatography (10% EtOAc/hex) to give 5-(2-thienyl)-2-dimethylaminopyridine (0.3 g, 29%): TLC (10% EtOAc/hex) Rf 0.24; HPLC ES-MS m/z (relative abundance) 205 (MH+, 100%).

Workup

  1. temperaturethe reaction mixture was heated at the reflux temperature for 2 h
  2. temperaturethe reaction was heated at the reflux temperature for 11 h
  3. temperatureto cool to room temperature
  4. extractionextracted with EtOAc (3×30 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by flash chromatography (10% EtOAc/hex)

Sources & evidence

ORD record
ord-4d2b9cdea0ab4f9d94dc5b9b63f2b98b
Source dataset
uspto-grants-2004_08
Patent number
US06784167B2

Reaction notes

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