Sodium Carbonate → HCID 67261890, compound

HRID 2359032Notes

Reaction equation

HRID 2359032 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]2[C:11]([C:12]3[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=3)=[CH:10][NH:9][N:8]=2)=[CH:4][CH:3]=1.[CH:18]1(B(O)O)[CH2:20][CH2:19]1.C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[NH4+]>ClC(Cl)C.C([O-])(=O)C.[Cu+2].C([O-])(=O)C.O>[CH:18]1([N:9]2[CH:10]=[C:11]([C:12]3[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=3)[C:7]([C:5]3[S:6][C:2]([Cl:1])=[CH:3][CH:4]=3)=[N:8]2)[CH2:20][CH2:19]1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 25517Ammonium ChlorideHCID 2760897Cyclopropylboronic acidHCID 178477995HCID 178477995, compound

Product 1

HCID 67261890HCID 67261890, compoundYield 25%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 962WaterSolventHCID 63651,1-DichloroethaneSolvent2×

Conditions

Temperature
70 °C

Procedure

To a suspension of 4-[3-(5-chloro-2-thienyl)-1H-pyrazol-4-yl]pyridine (0.57 mmol), cyclopropylboronic acid (1.14 mmol) and sodium carbonate (1.14 mmol) in 2 mL of dichloroethane, was added a suspension of copper acetate (0.57 mmol) and 2,2′-bipyridyn (0.57 mmol) in 4 mL of hot dichloroethane. The mixture was warmed up to 70° C. and stirred for 3 h under air. The resulting mixture was cooled to room temperature, and a saturated ammonium chloride solution was added, followed by water. The organic layer was separated, and the aqueous layer was extracted with dichloromethane. The combined organic layers were washed with brine, dried with MgSO4, and concentrated under reduced pressure. The residue was purified by chromatography on basic alumina (heptane/ethyl acetate 20:1 to 10:1) to afford 43 mg (24% yield) of 4-[1-cyclopropyl-3-(5-chloro-2-thienyl)-1H-pyrazol-4-yl]pyridine.

Workup

  1. additionwas added
  2. temperatureThe resulting mixture was cooled to room temperature
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with dichloromethane
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried with MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by chromatography on basic alumina (heptane/ethyl acetate 20:1 to 10:1)

Sources & evidence

ORD record
ord-146ba8b8a4cd42d5a75a0d8932ca2609
Source dataset
uspto-grants-2014_04
Patent number
US08685974B2

Reaction notes

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