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

HRID 1619119ノート

反応式

HRID 1619119 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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 30, 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. 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.

後処理

  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
  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

出典と根拠

ORDレコード
ord-a3b66315fc8d41b3893285b575059854
出典データセット
uspto-grants-2014_07
特許番号
US08772288B2

反応ノート

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