Iodine → 2-benzyl 5-methyl 6-iodo-1,3-dihydro-2H-isoindole-2,5-dicarboxylate

HRID 604631노트

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HRID 604631 반응식
N[C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][N:7]([C:11]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[O:12])[CH2:8]2)=[CH:4][C:3]=1[C:21]([O:23][CH3:24])=[O:22].N(OC(C)(C)C)=O.[I:32]I>C(Cl)(Cl)Cl>[I:32][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][N:7]([C:11]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[O:12])[CH2:8]2)=[CH:4][C:3]=1[C:21]([O:23][CH3:24])=[O:22]

참가 물질

5

반응물 3

HCID 807IodineHCID 10906Tert-Butyl nitriteHCID 670576842-benzyl 5-methyl 6-amino-1,3-dihydro-2H-isoindole-2,5-dicarboxylate

생성물 1

HCID 670577412-benzyl 5-methyl 6-iodo-1,3-dihydro-2H-isoindole-2,5-dicarboxylate

시약·촉매·용매 1

HCID 6212Chloroform용매

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온도
80 °C

실험 절차

To a solution of 2-benzyl 5-methyl 6-amino-1,3-dihydro-2H-isoindole-2,5-dicarboxylate (149 mg, 0.456 mmol) in CHCl3 (5 mL) was added t-butyl nitrite (108 uL, 0.912 mmol). The mixture was stirred for 20 min. I2 (34.7 mg, 1.37 mmol) was added and the resulting mixture was stirred at room temperature for 15 min. The mixture was then heated at 80° C. overnight. The reaction was quenched with sat. aq. NaHSO3 and extracted with CH2Cl2 (3×). The combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel to provide 2-benzyl 5-methyl 6-iodo-1,3-dihydro-2H-isoindole-2,5-dicarboxylate. LCMS calc.=438.0; found=437.8 (M+H)+. 1H NMR (500 MHz, CDCl3): δ 7.94-7.88 (2 s, 1H); 7.77-7.71 (2 s, 1H); 7.44-7.32 (m, 5H); 5.25 (s, 2-H); 4.76 (t, J=11.6 Hz, 4H); 3.98-3.94 (2 s, 3H).

후처리

  1. stirringthe resulting mixture was stirred at room temperature for 15 min
  2. customThe reaction was quenched with sat. aq. NaHSO3
  3. extractionextracted with CH2Cl2 (3×)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-7d5c2e2a43b64d62aed77c2ab0b915c3
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07910592B2

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