HCID 11632092, compound → HCID 11530111, compound

HRID 2104105Notes

Reaction equation

HRID 2104105 reaction equation
Cl[C:2]1[N:7]=[C:6]2[S:8][CH:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[C:5]2=[C:4]([NH:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[CH:3]=1>C(O)(=O)C.[Zn]>[F:17][C:14]1[CH:13]=[CH:12][C:11]([C:10]2[C:5]3[C:6](=[N:7][CH:2]=[CH:3][C:4]=3[NH:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)[S:8][CH:9]=2)=[CH:16][CH:15]=1

Participants

4

Reactant 1

HCID 11632092HCID 11632092, compound

Product 1

HCID 11530111HCID 11530111, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

[6-Chloro-3-(4-fluoro-phenyl)-thieno[2,3-b]pyridin-4-yl]-pyridin-2-ylmethyl-amine (40 mg, 0.1 mmol) was dissolved in acetic acid (3 ml). Zinc powder (71 mg, 1 mmol) was added and the mixture refluxed for 6 hr. On cooling, the mixture was filtered through celite and the solids washed with further portions of acetic acid (3×5 ml). The acetic acid extracts were neutralized with saturated sodium bicarbonate solution and extracted with DCM (2×50ml). The extracts were combined, dried over sodium sulfate and concentrated. The residue was purified on silica (ethyl actetate/hexane 20-40%) to give [3-(4-fluoro-phenyl)-thieno[2,3-b]pyridin-4-yl]-pyridin-2-ylmethyl-amine as a white solid. Yield=5.5 mg (15.2%).

Workup

  1. temperaturethe mixture refluxed for 6 hr
  2. temperatureOn cooling
  3. filtrationthe mixture was filtered through celite
  4. washthe solids washed with further portions of acetic acid (3×5 ml)
  5. extractionextracted with DCM (2×50ml)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified on silica (ethyl actetate/hexane 20-40%)

Sources & evidence

ORD record
ord-814ef95f49054160a18f46522896e93a
Source dataset
uspto-grants-2009_08
Patent number
US07576212B2

Reaction notes

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