Triethylamine → HCID 66671289, compound

HRID 1505631Notes

Reaction equation

HRID 1505631 reaction equation
[Br:1][C:2]1[C:6]2[C:7](Cl)=[N:8][CH:9]=[CH:10][C:5]=2[S:4][CH:3]=1.[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][NH2:19].C(N(CC)CC)C>CCO>[Br:1][C:2]1[C:6]2[C:7]([NH:19][CH2:18][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][N:12]=3)=[N:8][CH:9]=[CH:10][C:5]=2[S:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 195092-PyridinemethanamineHCID 184507733-Bromo-4-chlorothieno(3,2-c)pyridine

Product 1

HCID 66671289HCID 66671289, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Bromo-4-chloro-thieno[3,2-c]pyridine (409 mg, 16.5 mmol) was dissolved in anhydrous EtOH (20 ml), and 2-picolylamine (184 μl, 17.9 mmol) and triethylamine (241 μl, 17.3 mmol) were added. The reaction was heated to reflux and this was maintained for 24 h. The reaction was then allowed to cool to room temperature. The solvent was removed in vacuo and the residue partitioned between DCM (20 ml) and a saturated sodium, chloride solution (20 ml). The organic layer was dried (MgSO4), filtered and the solvent removed in vacuo. The crude residue was subjected to flash column chromatography (eluent petroleum spirit 40-60° C.:EtOAc, 3:1, Rf 0.3). This afforded the title compound as a yellow solid (236 mg, 44%).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux
  3. temperaturethis was maintained for 24 h
  4. customThe solvent was removed in vacuo
  5. customthe residue partitioned between DCM (20 ml)
  6. dry with materialThe organic layer was dried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent removed in vacuo
  9. customwas subjected to flash column chromatography (eluent petroleum spirit 40-60° C.:EtOAc, 3:1, Rf 0.3)

Sources & evidence

ORD record
ord-f5ff4d188278470fad459c76ef3b6164
Source dataset
uspto-grants-2015_12
Patent number
US09216992B2

Reaction notes

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