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 599348ノート

反応式

HRID 599348 の反応式
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

参加物

9

反応物 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

生成物 1

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

試薬・触媒・溶媒 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-phenylaniline触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d8ff008357d449e998e536870a537950
出典データセット
uspto-grants-2011_03
特許番号
US07897773B2

反応ノート

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