Benzo(B)Thiophene-2-Boronic Acid → HCID 54055743, compound

HRID 1837936Notes

Reaction equation

HRID 1837936 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][C:15]1[CH:24]=[CH:23][C:22]2[CH2:21][CH2:20][CH2:19][NH:18][C:17]=2[N:16]=1)([CH3:4])([CH3:3])[CH3:2].[S:34]1[C:38](B(O)O)=[CH:37][C:36]2[CH:42]=[CH:43][CH:44]=[CH:45][C:35]1=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]=[C:8]([C:38]1[S:34][C:35]2[CH:45]=[CH:44][CH:43]=[CH:42][C:36]=2[CH:37]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:24]=[CH:23][C:22]2[CH2:21][CH2:20][CH2:19][NH:18][C:17]=2[N:16]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

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

Product 1

HCID 54055743HCID 54055743, compound

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-90c1fd48d5c54285a9c834282b188f1a
Source dataset
uspto-grants-2004_08
Patent number
US06784190B2

Reaction notes

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