Sodium Carbonate → HCID 57516640, compound

HRID 1898606Notes

Reaction equation

HRID 1898606 reaction equation
[C:1]1(B2OC(C)(C)C(C)(C)O2)[CH2:5][CH2:4][CH2:3][CH:2]=1.[Cl:15][C:16]1[CH:21]=[C:20](I)[CH:19]=[CH:18][N:17]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:15][C:16]1[CH:21]=[C:20]([C:1]2[CH2:5][CH2:4][CH2:3][CH:2]=2)[CH:19]=[CH:18][N:17]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 15165112-Chloro-4-iodopyridineHCID 154866112-(Cyclopent-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 57516640HCID 57516640, compoundYield 86%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2-cyclopentenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (681 mg, 3.51 mmol) and 2-chloro-4-iodopyridine (700 mg, 2.92 mmol) in 1,4-dioxane (12 mL) was added 2.0 M aqueous Na2CO3 (4.39 mL, 8.77 mmol) and tetrakis(triphenylphosphine)palladium(0) (67.6 mg, 0.059 mmol). The reaction mixture was heated at 90° C. for 3.5 h then cooled to room temperature, diluted with water and extracted with EtOAc (2×). The combined organics were dried over MgSO4 and concentrated. The residue was purified by silica gel chromatography (0% to 10% EtOAc/hexanes) to afford 450 mg (86%) of 2-chloro-4-cyclopent-1-enyl-pyridine as a white solid.

Workup

  1. temperaturethen cooled to room temperature
  2. extractionextracted with EtOAc (2×)
  3. dry with materialThe combined organics were dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (0% to 10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-7e8d6c69c3394c85acfd0b408031ddf6
Source dataset
uspto-grants-2013_08
Patent number
US08518945B2

Reaction notes

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