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

HRID 2096967노트

반응식

HRID 2096967 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-98865af5bb2a408d8d28bca12e90ffc1
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08450341B2

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