5-Chlorooxindole → 3-(5-Amino-3H-isobenzofuran-1-ylidene)-5-chloro-1,3-dihydro-indol-2-one

HRID 1263723노트

반응식

HRID 1263723 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.C[Si](C)(C)N[Si](C)(C)C.[Na].[NH2:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[C:28](=O)[O:27][CH2:26]2>C(COC)OC.CN(C=O)C>[NH2:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[C:28](=[C:5]1[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([Cl:1])[CH:3]=3)[NH:7][C:6]1=[O:11])[O:27][CH2:26]2

참가 물질

6

반응물 3

HCID 1528015-ChlorooxindoleHCID 7206695-AminophthalideHCID 45051731Sodium hexamethyidisilazane

생성물 1

HCID 696591863-(5-Amino-3H-isobenzofuran-1-ylidene)-5-chloro-1,3-dihydro-indol-2-one수율 31.3%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 80711,2-Dimethoxyethane용매

실험 절차

To a solution of 5-chlorooxindole (0.629 g, 3.78 mmol) in 10.0 mL monoglyme was added 7.51 mL sodium hexamethyldisilazane (1.0 M in THF) over 3 min. After stirring a troom temperature for 8 min, a solution of 5-aminophthalide (0.561 g, 3.78 mmol) in 3.0 mL of DMF was added over 1 min. The mixture was stirred for 40 min and then quenched into 4% aqueous HCl solution. The aqueous solution was neutralized to pH 7 with 1 M NaOH and then made basic with saturated NaHCO3. The solid was filtered and washed with H2O and then partitioned between EtOAc and saturated NaHCO3 (heated to dissolve the solid). The organic phase was washed with H2O, brine and then dried with Na2SO4. The solvent was removed in vacuo and the residue triturated with MeOH to give the title compound (353 mg, 31%) as a yellow solid.

후처리

  1. stirringThe mixture was stirred for 40 min
  2. customquenched into 4% aqueous HCl solution
  3. filtrationThe solid was filtered
  4. washwashed with H2O
  5. custompartitioned between EtOAc and saturated NaHCO3 (
  6. temperatureheated
  7. dissolutionto dissolve the solid)
  8. washThe organic phase was washed with H2O, brine
  9. dry with materialdried with Na2SO4
  10. customThe solvent was removed in vacuo
  11. customthe residue triturated with MeOH

출처 및 근거

ORD 기록
ord-0a9ff420ed364d2eadde5c3176458fca
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06541504B1

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