2,6-Dichloropyridine → HCID 89401681, compound

HRID 573992Notes

Reaction equation

HRID 573992 reaction equation
Cl.[F:2][C:3]1[CH:4]=[CH:5][C:6]([C@@H:9]([NH2:11])[CH3:10])=[N:7][CH:8]=1.[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15](Cl)[N:14]=1>>[Cl:12][C:13]1[N:14]=[C:15]([NH:11][C@H:9]([C:6]2[CH:5]=[CH:4][C:3]([F:2])=[CH:8][N:7]=2)[CH3:10])[CH:16]=[CH:17][CH:18]=1

Participants

3

Reactant 2

HCID 169892,6-DichloropyridineHCID 67123789(S)-1-(5-fluoropyridin-2-yl)ethanamine hydrochloride

Product 1

HCID 89401681HCID 89401681, compoundYield 36.8%

Procedure

(S)-1-(5-Fluoropyridin-2-yl)ethanamine hydrochloride (prepared as described in WO2006/123113, 0.291 g, 1.37 mmol) was added to a solution of 2,6-dichloropyridine (0.203 g, 1.38 mmol) in NN-diisopropylethylamine (1.2 mL, 6.89 mmol) and the resulting mixture was stirred and heated to reflux for two days. The solvent was evaporated under reduced pressure and the residue was purified by flash chromatography (0-10% ethyl acetate in hexanes) to yield the title compound (127 mg, 36%) as a yellow solid.

Workup

  1. temperatureheated
  2. temperatureto reflux for two days
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by flash chromatography (0-10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-195a6097e4af416585a272aec3dce1df
Source dataset
uspto-grants-2015_05
Patent number
US09034311B2

Reaction notes

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