Ethanol → HCID 59834389, compound

HRID 271079Notes

Reaction equation

HRID 271079 reaction equation
[F:1][C:2]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:3]=1[O:4][C:5]1[CH:6]=[C:7](F)[C:8]([C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19][CH3:20])=O)=[N:9][CH:10]=1.CCO.C(N(CC)C(C)C)(C)C.[NH2:39][NH2:40]>CCOC(C)=O>[F:1][C:2]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:3]=1[O:4][C:5]1[CH:6]=[C:7]2[NH:40][N:39]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[O:19][CH3:20])[C:8]2=[N:9][CH:10]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 9321HydrazineHCID 81531DiisopropylethylamineHCID 59834372HCID 59834372, compound

Product 1

HCID 59834389HCID 59834389, compoundYield 5.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

[5-(2,4-Difluoro-phenoxy)-3-fluoro-pyridin-2-yl]-(2-methoxy-phenyl)-methanone (560 mg, 1.5 mmol) was added to 17 mL of EtOH and the reaction mixture was heated until all solid had dissolved. The reaction mixture was cooled, and (N,N-diisopropyl)ethylamine (0.21 mL, 2.3 mmol) and hydrazine (0.1 mL, 3.1 mmol) were added. The reaction mixture was stirred for four hours at room temperature, and then was taken up in 60 mL of EtOAc, washed four times with 20 mL of water, dried (MgSO4). The organic solvent was filtered and concentrated under reduced pressure. The residue was purified by flash chromatography 40 mm×7.5 cm) with 4: to 1:1 hexanes/EtOAc to yield 0.03 g of 6-(2,4-difluoro-phenoxy)-3-(2-methoxy-phenyl)-1H-pyrazolo[4,3-b]pyridine. Mass Spec. M+H=354.

Workup

  1. temperaturethe reaction mixture was heated until all solid
  2. dissolutionhad dissolved
  3. temperatureThe reaction mixture was cooled
  4. washwashed four times with 20 mL of water
  5. dry with materialdried (MgSO4)
  6. filtrationThe organic solvent was filtered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash chromatography 40 mm×7.5 cm) with 4

Sources & evidence

ORD record
ord-ed9396ba9822492590503d684788389f
Source dataset
uspto-grants-2008_11
Patent number
US07452880B2

Reaction notes

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