Benzo(B)Thiophene-2-Boronic Acid → tert-Butyl non-2-enoate

HRID 379279Notes

Reaction equation

HRID 379279 reaction equation
[C:1]([O:5][C:6](=[O:33])[CH:7]=[C:8](OS(C(F)(F)F)(=O)=O)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]C1C=CC2CCCNC=2N=1)([CH3:4])([CH3:3])[CH3:2].S1C(B(O)O)=CC2C=CC=CC1=2.C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:33])[CH:7]=[CH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 2359Benzo(B)Thiophene-2-Boronic AcidHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 54554919HCID 54554919, compound

Product 1

HCID 71339527tert-Butyl non-2-enoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
95 °C

Procedure

To a stirred solution of 9-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-3-(trifluoromethanesulfonyloxy)-non-2-enoic acid tert-butyl ester 29-6 (100 mg, 0.20 mmol) in toluene (2.5 mL) was added palladium(tetrakis)-triphenylphosphine (23 mg, 0.020 mmol), benzo[b]thiophene-2-boronic acid (50 mg, 0.41 mmol) and potassium carbonate (56 mg, 0.41 mmol). The resulting suspension was heated at 90-100° C. for 2 hours, and then was allowed to cool to ambient temperature. The reaction mixture was then poured into saturated aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried with anhydrous magnesium sulfate, filtered, and concentrated at reduced pressure. The resulting oil was purified by flash column chromatography over silica gel with 4:1 ethyl acetate/hexanes to give 29-7b as a colorless oil.

Workup

  1. temperatureto cool to ambient temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium chloride
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated at reduced pressure
  7. customThe resulting oil was purified by flash column chromatography over silica gel with 4:1 ethyl acetate/hexanes

Sources & evidence

ORD record
ord-1ebe88b2581246b2838232f651cafeeb
Source dataset
uspto-grants-2001_10
Patent number
US06297249B1

Reaction notes

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