Potassium Carbonate → 2-[4-[(1E)-1-phenylmethoxyimino-2,3-dihydroinden-5-yl]-3-pyridin-4-ylpyrazol-1-yl]ethanol

HRID 1726397Notes

Reaction equation

HRID 1726397 reaction equation
Br[C:2]1[C:3]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[N:4][N:5]([CH2:7][CH2:8][OH:9])[CH:6]=1.[CH2:16]([O:23]/[N:24]=[C:25]1\[CH2:26][CH2:27][C:28]2[C:33]\1=[CH:32][CH:31]=[C:30](B(O)O)[CH:29]=2)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O>[CH2:16]([O:23]/[N:24]=[C:25]1\[CH2:26][CH2:27][C:28]2[C:33]\1=[CH:32][CH:31]=[C:30]([C:2]1[C:3]([C:10]3[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=3)=[N:4][N:5]([CH2:7][CH2:8][OH:9])[CH:6]=1)[CH:29]=2)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 672937372-(4-bromo-3-(pyridin-4-yl)-1H-pyrazol-1-yl)ethanolHCID 87623866[(1E)-1-phenylmethoxyimino-2,3-dihydroinden-5-yl]boronic acid2×

Product 1

HCID 876234382-[4-[(1E)-1-phenylmethoxyimino-2,3-dihydroinden-5-yl]-3-pyridin-4-ylpyrazol-1-yl]ethanolYield 69.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To 2-(4-bromo-3-(pyridin-4-yl)-1H-pyrazol-1-yl)ethanol (100 mg; Example 4, step 3) in 7 mL acetonitrile and 3 mL water, was added 136 mg (E)-1-(benzyloxyimino)-2,3-dihydro-1H-inden-5-ylboronic acid (product of Example 2, Step 4), and 155 mg potassium carbonate. The mixture was purged with nitrogen and about 43 mg tetrakis(triphenyphosphine)palladium(0) catalyst was added. The mixture was heated at 80° C. After 1 hour, the reaction mixture was filtered through celite, the filter cake washed with ethyl acetate, and filtrate evaporated under vacuum. The residue was purified by chromatography, eluting with a mixture of 8:1 ethyl acetate-methanol to afford 110 mg (69% yield) product as a white solid. 1H NMR (CDCl3) was consistent with the desired structure. LC/MS showed one peak with a M+1 molecular ion of m/z 425.2 by positive ESI.

Workup

  1. customThe mixture was purged with nitrogen and about 43 mg tetrakis(triphenyphosphine)palladium(0) catalyst
  2. additionwas added
  3. filtrationthe reaction mixture was filtered through celite
  4. washthe filter cake washed with ethyl acetate, and filtrate
  5. customevaporated under vacuum
  6. customThe residue was purified by chromatography
  7. washeluting with a mixture of 8:1 ethyl acetate-methanol

Sources & evidence

ORD record
ord-0e5a133cddc44114b3925d46895c6a00
Source dataset
uspto-grants-2009_02
Patent number
US07491829B2

Reaction notes

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