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

HRID 604631ノート

反応式

HRID 604631 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-7d5c2e2a43b64d62aed77c2ab0b915c3
出典データセット
uspto-grants-2011_03
特許番号
US07910592B2

反応ノート

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