Potassium Carbonate → 2-[3-(5-Bromo-pyridin-2-yl)-propyl]-isoindole-1,3-dione

HRID 993241

反応式

HRID 993241 の反応式
[CH2:1]([N:4]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]1=[O:14])[CH:2]=[CH2:3].B1C2CCCC1CCC2.C([O-])([O-])=O.[K+].[K+].Br[C:31]1[CH:36]=[CH:35][C:34]([Br:37])=[CH:33][N:32]=1>CN(C=O)C.C(OCC)(=O)C.CC([O-])=O.CC([O-])=O.[Pd+2].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[Br:37][C:34]1[CH:35]=[CH:36][C:31]([CH2:3][CH2:2][CH2:1][N:4]2[C:12](=[O:13])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]2=[O:14])=[N:32][CH:33]=1

参加物

9

反応物 4

HCID 11430Potassium CarbonateHCID 693532,5-DibromopyridineHCID 789669-Borabicyclo(3.3.1)nonaneHCID 224401N-Allylphthalimide

生成物 1

HCID 184089632-[3-(5-Bromo-pyridin-2-yl)-propyl]-isoindole-1,3-dione収率 37.3%

試薬・触媒・溶媒 4

HCID 167845palladium(II) acetate触媒HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a stirred solution of 2-allyl-isoindole-1,3-dione (3-1) (18.9 g, 101 mmol) in degassed TBF (100 mL) at 0° C. was added dropwise a solution of 9-BBN (243 mL of 0.5M in THF, 121 mmol) and the mixture stirred for 18 hours at ambient temperature. K2CO3 (24 g, 172 mmol) and 2,5-dibromopyridine (30 g, 126 mmol) were added, followed by a premixed and aged (70° C. for 30 min) suspension of Pd(OAc)2 (2.6 g, 11.5 mmol) and DPPF (7 g, 12.6 mmol) in degassed DMF (100 mL). The resulting mixture was stirred for 18 hours at 70° C., cooled, diluted with ethyl acetate, washed with water and brine, dried over MgSO4, and concentrated. To the stirring residue dissolved in TUF (500 mL) were added water (150 mL) and NaHCO3 (33 g) and after 10 minutes, NaBO3•H2O (55 g). After vigorous stirring for 30 minutes, the mixture was diluted with ethyl acetate, washed with water and brine, dried over MgSO4, and concentrated to an oil. The residue was chromatographed on silica gel (10-20% EtOAc/hexane) to give 13 g of 3-2 as a colorless oil.

後処理

  1. additiona premixed
  2. stirringThe resulting mixture was stirred for 18 hours at 70° C.
  3. temperaturecooled
  4. washwashed with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. dissolutionTo the stirring residue dissolved in TUF (500 mL)
  8. additionwere added water (150 mL) and NaHCO3 (33 g)
  9. waitafter 10 minutes
  10. stirringAfter vigorous stirring for 30 minutes
  11. additionthe mixture was diluted with ethyl acetate
  12. washwashed with water and brine
  13. dry with materialdried over MgSO4
  14. concentrationconcentrated to an oil
  15. customThe residue was chromatographed on silica gel (10-20% EtOAc/hexane)

出典と根拠

ORDレコード
ord-d63b5ea7295c47c4b392779471d1970b
出典データセット
uspto-grants-2002_10
特許番号
US06472403B2

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