Dimethyl Sulfoxide → (2'-Oxo-1',2'-dihydrospiro[oxane-4,3'-pyrrolo[3,2-b]pyridin]-6'-yl)boronic acid

HRID 2096967Notes

Reaction equation

HRID 2096967 reaction equation
Br[C:2]1[CH:3]=[C:4]2[NH:10][C:9](=[O:11])[C:8]3([CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)[C:5]2=[N:6][CH:7]=1.[B:17]1(B2OC(C)(C)C(C)(C)O2)[O:21]C(C)(C)C(C)(C)[O:18]1.C([O-])(=O)C.[K+].CS(C)=O>C(OCC)(=O)C>[O:11]=[C:9]1[NH:10][C:4]2[C:5](=[N:6][CH:7]=[C:2]([B:17]([OH:21])[OH:18])[CH:3]=2)[C:8]21[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 669543106'-Bromo-1',2'-dihydrospiro[oxane-4,3'-pyrrolo[3,2-b]pyridine]-2'-one

Product 1

HCID 66954044(2'-Oxo-1',2'-dihydrospiro[oxane-4,3'-pyrrolo[3,2-b]pyridin]-6'-yl)boronic acid

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

An oven dried resealable Schlenk tube was charged with 6′-bromo-2,3,5,6-tetrahydrospiro[pyran-4,3′-pyrrolo[3,2-b]pyridin]-2′(1′H)-one (preparation 16, 0.350 g, 1.24 mmol), bis(pinacolato)diboron (0.470 g, 1.85 mmol), potassium acetate (0.240 g, 2.48 mmol) and dimethylsulphoxide (4 mL). The Schlenk tube was subjected to three cycles of evacuation-backfilling with argon, and 1,1′-bis(diphenylphosphino)ferrocene-palladium(II) dichloride dichloromethane complex (0.06 g, 0.07 mmol) was added. After three further cycles of evacuation-backfilling with argon, the Schlenk tube was capped and placed in an oil bath at 110° C. After 16 hours, the mixture was cooled and ethyl acetate was added and the organic layer was extracted with 2M aqueous hydrochloric acid solution. The aqueous phase was washed with ethyl acetate and then the pH of the solution was adjusted to 6 with 6M aqueous sodium hydroxide solution and extracted with ethyl acetate. The organic layer was dried (MgSO4) and evaporated to give the title compound in quantitative yield as a brown oily residue, which was used without further purification.

Workup

  1. customAn oven dried resealable Schlenk tube
  2. additionwas added
  3. customAfter three further cycles of evacuation-backfilling with argon, the Schlenk tube was capped
  4. customplaced in an oil bath at 110° C
  5. temperaturethe mixture was cooled
  6. extractionthe organic layer was extracted with 2M aqueous hydrochloric acid solution
  7. washThe aqueous phase was washed with ethyl acetate
  8. extractionextracted with ethyl acetate
  9. dry with materialThe organic layer was dried (MgSO4)
  10. customevaporated

Sources & evidence

ORD record
ord-98865af5bb2a408d8d28bca12e90ffc1
Source dataset
uspto-grants-2013_05
Patent number
US08450341B2

Reaction notes

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