Sodium Bicarbonate → HCID 23434084, compound

HRID 2121726Notes

Reaction equation

HRID 2121726 reaction equation
Cl[C:2]1[S:3][C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[F:17])=[C:5]2[C:9](=[O:10])[CH2:8][CH2:7][C:6]=12.[N:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.C([O-])(O)=O.[Na+]>COCCOC.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[F:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:4]1[S:3][C:2]([C:21]2[CH:22]=[CH:23][N:18]=[CH:19][CH:20]=2)=[C:6]2[CH2:7][CH2:8][C:9](=[O:10])[C:5]=12

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 23434091HCID 23434091, compound

Product 1

HCID 23434084HCID 23434084, compoundYield 91.2%

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a stirred solution of 1-chloro-3-(2-fluorophenyl)-5,6-dihydro-4H-cyclopenta(c)thiophene-4-one (118 mg, 0.443 mmol) in DME (7.5 mL) was added 4-pyridineboronic acid (130 mg, 1.06 mmol), saturated aqueous NaHCO3 solution (2.5 mL) and bis(triphenylphosphine)palladium(II)chloride (100 mg, 0.14 mmol) at room temperature under nitrogen. The mixture was heated at reflux temperature for 20 hours. The whole was extracted with ethyl acetate (50 mL×2), and the combined organic layers were washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography eluting with hexane-ethyl acetate (1:1) to provide the title product (125 mg, 91% yield).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux temperature for 20 hours
  3. extractionThe whole was extracted with ethyl acetate (50 mL×2)
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography
  8. washeluting with hexane-ethyl acetate (1:1)

Sources & evidence

ORD record
ord-5c88eaf4d24a4b9f92c85ef06bd32be2
Source dataset
uspto-grants-2004_02
Patent number
US06696470B2

Reaction notes

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