1,4-Dioxane → 1-[(3-Pyridin-3-yl-8-azabicyclo[3.2.1]oct-2-en-8-yl)carbonyl]-1,2,3,4-tetrahydroquinoline

HRID 599348노트

반응식

HRID 599348 반응식
FC(F)(F)S(O[C:7]1[CH2:13][CH:12]2[NH:14][CH:9]([CH2:10][CH2:11]2)[CH:8]=1)(=O)=O.CC1(C)C(C)(C)OB([C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)O1.[Cl-].[Li+].P([O-])([O-])([O-])=O.[K+].[K+].[K+].[O:42]1[CH2:47]COCC1>CN(C1C(C2[C-]=CC=CC=2)=CC=CC=1)C.C1[C@H]2CC(PC3[C@H]4C[C@H](CC4)C3)[C@H](C2)C1.Cl[Pd+].C(OCC)(=O)C.O>[N:27]1[CH:28]=[CH:29][CH:30]=[C:25]([C:7]2[CH2:13][CH:12]3[N:14]([C:47]([N:27]4[C:26]5[C:25](=[CH:13][CH:7]=[CH:8][CH:9]=5)[CH2:30][CH2:29][CH2:28]4)=[O:42])[CH:9]([CH2:10][CH2:11]3)[CH:8]=2)[CH:26]=1

참가 물질

9

반응물 5

HCID 312751,4-DioxaneHCID 62657Potassium Phosphate, TribasicHCID 433294Lithium ChlorideHCID 27346563-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 866321818-Azabicyclo[3.2.1]oct-2-ene-3-yl trifluoromethanesulfonate

생성물 1

HCID 248046411-[(3-Pyridin-3-yl-8-azabicyclo[3.2.1]oct-2-en-8-yl)carbonyl]-1,2,3,4-tetrahydroquinoline

시약·촉매·용매 3

HCID 11272965[(1R,4S)-2-Bicyclo[2.2.1]heptanyl]-[(1S,4R)-2-bicyclo[2.2.1]heptanyl]phosphane;chloropalladium(1+);N,N-dimethyl-2-phenylaniline촉매HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

0.5 g of dihydroquinolin-1(2H)-ylcarbonyl)-8-azabicyclo[3.2.1]oct-2-ene-3-yl trifluoromethanesulfonate, 0.419 g of 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine, 0.1 g of lithium chloride, 0.765 g of potassium phosphate, 0.067 g of 2′-(dimethylamino)-2-biphenylpalladium(II)chloride dinorbornylphosphine and 4.3 ml of dioxane are introduced into a 10 ml glass tube. The tube is sealed, and then heated at 100° C. under microwave radiation for 50 minutes. Water and ethyl acetate are added. The aqueous phase is extracted three times with ethyl acetate. The organic phases are combined, dried over sodium sulfate and the solvent is evaporated off under reduced pressure. The residue is chromatographed on silica gel with a 3/7 mixture of heptane/ethyl acetate. 0.3 g of 1-[(3-pyridin-3-yl-8-azabicyclo[3.2.1]oct-2-en-8-yl)carbonyl]-1,2,3,4-tetrahydroquinoline is obtained.

후처리

  1. customThe tube is sealed
  2. extractionThe aqueous phase is extracted three times with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. customthe solvent is evaporated off under reduced pressure
  5. customThe residue is chromatographed on silica gel with a 3/7 mixture of heptane/ethyl acetate

출처 및 근거

ORD 기록
ord-d8ff008357d449e998e536870a537950
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07897773B2

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