Iodine → (Rac)-2-[(8-iodo-2,3,5,6-tetrahydro[1,4]oxazino[2,3,4-hi]indol-6-yl)methyl]-1h-isoindole-1,3(2h)-dione

HRID 2179905Notes

Reaction equation

HRID 2179905 reaction equation
[O:1]1[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH:6]([CH2:13][N:14]2[C:22](=[O:23])[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[C:15]2=[O:24])[CH2:5][N:4]3[CH2:3][CH2:2]1.[I:25]I>C(Cl)(Cl)Cl.FC(F)(F)C([O-])=O.[Ag+]>[I:25][C:9]1[CH:8]=[C:7]2[C:12]3=[C:11]([O:1][CH2:2][CH2:3][N:4]3[CH2:5][CH:6]2[CH2:13][N:14]2[C:22](=[O:23])[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]2=[O:24])[CH:10]=1

Participants

5

Reactant 2

HCID 807Iodine3×HCID 22488989(Rac)-2-(2,3,5,6-tetrahydro[1,4]oxazino[2,3,4-hi]indol-6-ylmethyl)-1h-isoindole-1,3(2h)-dione

Product 1

HCID 22488988(Rac)-2-[(8-iodo-2,3,5,6-tetrahydro[1,4]oxazino[2,3,4-hi]indol-6-yl)methyl]-1h-isoindole-1,3(2h)-dione

Reagents, catalysts & solvents 2

HCID 76299Silver trifluoroacetateCatalyst3×HCID 6212ChloroformSolvent4×

Procedure

To a suspension of (rac)-2-(2,3,5,6-tetrahydro[1,4]oxazino[2,3,4-hi]indol-6-ylmethyl)-1H-isoindole-1,3(2H)-dione (0.081 g, 0.253 mmol) and silver trifluoroacetate (0.059 g, 0.266 mmol) in CHCl3 (2.0 mL) was added a solution of iodine (0.067 g, 0.266 mmol) in CHCl3 (8.0 mL) dropwise at rt. The mixture was stirred for 68 h. Silver trifluoroacetate (0.03 g, 0.136 mmol) and solution of iodine (0.035 g, 0.136 mmol) in CHCl3 (6.0 mL) were added. The mixture was stirred at rt for 4 h and added again silver trifluoroacetate (0.02 g, 0.09 mmol) and solution of iodine (0.025 g, 0.10 mmol) in CHCl3 (5.0 mL). After stirring for another 2 h, the mixture was filtered through a pad of celite and washed with CHCl3. The filtrate was washed with Na2SO3 solution and dried (MgSO4). After filtration, the filtrate was concentrated in vacuo to dryness and the residue was subjected to prep TLC (EtOAc/hexane, 1:2) to give 0.046 g (41%) of light yellow oil as the title compound: 1H NMR (400 MHz, CDCl3) δ 7.81-7.78 (m, 2 H), 7.69-7.65 (m, 2 H), 6.98 (s, 1 H), 6.86 (s, 1 H), 4.34-4.29 (m, 2 H), 3.91-3.80 (m, 2 H), 3.62-3.58 (m, 1 H), 3.24-3.14 (m, 2 H), 3.04-3.00 (m, 1 H), 2.97-2.92 (m, 1 H); MS (EI) m/z 447 (M++H).

Workup

  1. stirringThe mixture was stirred at rt for 4 h
  2. stirringAfter stirring for another 2 h
  3. filtrationthe mixture was filtered through a pad of celite
  4. washwashed with CHCl3
  5. washThe filtrate was washed with Na2SO3 solution
  6. dry with materialdried (MgSO4)
  7. filtrationAfter filtration
  8. concentrationthe filtrate was concentrated in vacuo to dryness

Sources & evidence

ORD record
ord-fd83a39bb2f64da0bad86aba2afb8121
Source dataset
uspto-grants-2005_05
Patent number
US06887868B2

Reaction notes

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