Potassium Carbonate → 2-(3-{5-[4-(1,3-Dioxo-isoindol-2-yl)-butyl]-pyridin-2-yl}-propyl)-isoindole-1,3-dione

HRID 993243

반응식

HRID 993243 반응식
[CH2:1]([N:5]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15])[CH2:2][CH:3]=[CH2:4].B1C2CCCC1CCC2.C([O-])([O-])=O.[K+].[K+].Br[C:32]1[CH:33]=[CH:34][C:35]([CH2:38][CH2:39][CH2:40][N:41]2[C:49](=[O:50])[C:48]3[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=3)[C:42]2=[O:51])=[N:36][CH:37]=1>C1COCC1.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]>[O:15]=[C:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:13](=[O:14])[N:5]1[CH2:1][CH2:2][CH2:3][CH2:4][C:32]1[CH:33]=[CH:34][C:35]([CH2:38][CH2:39][CH2:40][N:41]2[C:42](=[O:51])[C:43]3[C:48](=[CH:47][CH:46]=[CH:45][CH:44]=3)[C:49]2=[O:50])=[N:36][CH:37]=1

참가 물질

10

반응물 4

HCID 11430Potassium CarbonateHCID 789669-Borabicyclo(3.3.1)nonaneHCID 339432N-(3-Buten-1-yl)phthalimideHCID 184089632-[3-(5-Bromo-pyridin-2-yl)-propyl]-isoindole-1,3-dione

생성물 1

HCID 184089852-(3-{5-[4-(1,3-Dioxo-isoindol-2-yl)-butyl]-pyridin-2-yl}-propyl)-isoindole-1,3-dione수율 76.2%

시약·촉매·용매 5

HCID 167845palladium(II) acetate촉매HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a stirred solution of 3-3 (9.1 g, 45.4 mmol) in degassed THF (50 mL) at 0° C. was added dropwise a solution of 9-BBN (110 mL of 0.5M in THF, 55 mmol) and the mixture stirred for 18 hours at ambient temperature. K2CO3 (10.8 g, 77.4 mmol) and 3-2 (5.0 g, 17.4 mmol) were added, followed by a premixed and aged (70° C. for 30 min) suspension of Pd(OAc)2 (1.2 g, 5.2 mmol) and DPPF (3.2 g, 5.6 mmol) in degassed DMF (50 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. The residue was chromatographed on silica gel (40-50% EtOAc/hexane) to give 6.2 g of 3-4 as a white solid.

후처리

  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. customThe residue was chromatographed on silica gel (40-50% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-9f0785b893714f97b5a4052808061b31
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06472403B2

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