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4-(4-bromo-1-methyl-1H-pyrazol-3-yl)pyridine → 5-(1-methyl-3-(pyridin-4-yl)-1H-pyrazol-4-yl)-2,3-dihydroinden-1-one O-benzyl oxime

HRID 1726395
Notes
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Reaction equation

HRID 1726395 reaction equation
[CH2:1]([O:8]/[N:9]=[C:10]1\[CH2:11][CH2:12][C:13]2[C:18]\1=[CH:17][CH:16]=[C:15](B(O)O)[CH:14]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:23]1[C:24]([C:29]2[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=2)=[N:25][N:26]([CH3:28])[CH:27]=1>C(#N)C.O>[CH2:1]([O:8][N:9]=[C:10]1[C:18]2[C:13](=[CH:14][C:15]([C:23]3[C:24]([C:29]4[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=4)=[N:25][N:26]([CH3:28])[CH:27]=3)=[CH:16][CH:17]=2)[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 689237284-(4-bromo-1-methyl-1H-pyrazol-3-yl)pyridineHCID 87623866[(1E)-1-phenylmethoxyimino-2,3-dihydroinden-5-yl]boronic acid

Product 1

HCID 866072785-(1-methyl-3-(pyridin-4-yl)-1H-pyrazol-4-yl)-2,3-dihydroinden-1-one O-benzyl oximeYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342
Acetonitrile
Solvent

Procedure

To (E)-1-(benzyloxyimino)-2,3-dihydro-1H-inden-5-ylboronic acid (3.00 g; Example 2, Step 4) in 32 mL acetonitrile and 8.0 mL water was added 4-(4-bromo-1-methyl-1H-pyrazol-3-yl)pyridine (2.00 g; Example 3, Step 3). The solution was deoxygenated by bubbling nitrogen through the solution for 10 min. To the resulting mixture was added 5.62 g potassium carbonate, 10 mL N,N-dimethylformamide, and 290 mg tetrakis(triphenyphosphine)palladium(0). The mixture was then refluxed for 8 hours (over the course of this time a small portion of catalyst was added twice). The cooled reaction mixture was filtered through celite and the filter cake was washed with ethyl acetate. The filtrate was washed with water, brine, dried over sodium sulfate, filtered, and evaporated under vacuum to yield 5.1 g crude product as an oil. The crude material was purified by chromatography, eluting with ethyl acetate to afford 2.50 g (80% yield) product as a light yellow foam. 1H NMR (CDCl3) was consistent with the desired structure. LC/MS showed one peak with a M+1 molecular ion of m/z 395.2 by positive ESI.

Workup

  1. customThe solution was deoxygenated
  2. customby bubbling nitrogen through the solution for 10 min
  3. additionTo the resulting mixture was added 5.62 g potassium carbonate, 10 mL N,N-dimethylformamide, and 290 mg tetrakis(triphenyphosphine)palladium(0)
  4. temperatureThe mixture was then refluxed for 8 hours (over the course of this time a small portion of catalyst
  5. additionwas added twice)
  6. customThe cooled reaction mixture
  7. filtrationwas filtered through celite
  8. washthe filter cake was washed with ethyl acetate
  9. washThe filtrate was washed with water, brine
  10. dry with materialdried over sodium sulfate
  11. filtrationfiltered
  12. customevaporated under vacuum
  13. customto yield 5.1 g crude product as an oil
  14. customThe crude material was purified by chromatography
  15. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-ec2bd62d60ba4f7e8abdbdee869fd061
Source dataset
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07491829B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes