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

HRID 604631Notes

Reaction equation

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]

Participants

Conditions

Temperature: 80 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-7d5c2e2a43b64d62aed77c2ab0b915c3
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07910592B2

Reaction notes

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