Sodium Iodide → 4-(2-Chlorophenyl)-8-(4-iodobutyl)-9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

HRID 11134Notes

Reaction equation

HRID 11134 reaction equation
FC(F)(F)S(O[CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[C:12]([O:36][CH3:37])=[CH:13][C:14]2[C:15]3[C:16]4[C:33](=[O:34])[NH:32][C:31](=[O:35])[C:17]=4[C:18]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[Cl:30])=[CH:19][C:20]=3[NH:21][C:22]=2[CH:23]=1)(=O)=O.[I-:40].[Na+]>C(OCC)(=O)C>[Cl:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[C:18]1[C:17]2[C:31](=[O:35])[NH:32][C:33](=[O:34])[C:16]=2[C:15]2[C:14]3[CH:13]=[C:12]([O:36][CH3:37])[C:11]([CH2:10][CH2:9][CH2:8][CH2:7][I:40])=[CH:23][C:22]=3[NH:21][C:20]=2[CH:19]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 219806854-[4-(2-Chlorophenyl)-9-methoxy-1,3-dioxo-1,2,3,6-tetrahydropyrrolo[3,4-c]carbazol-8-yl]butyl trifluoromethanesulfonate

Product 1

HCID 219809064-(2-Chlorophenyl)-8-(4-iodobutyl)-9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the mesylate (172) 0.12 g, 0.21 mmol) prepared as described in example 311 and sodium iodide (1 g) in ethyl acetate (50 mL) was refluxed for 4 h. The cooled solution was washed with water and worked up to give the iodide (173) which crystallised from tetrahydrofuran/petroleum ether as an orange powder (0.10 g, 85%), mp 142–144° C. 1H NMR δ [(CD3)2SO] 11.86 (s, 1H), 11.05 (s, 1H), 8.43 (s, 1H), 7.58 (m, 1H), 7.55 (s, 1H), 7.52–7.43 (m, 3H), 7.42 (s, 1H), 3.94 (s, 3H). EIMS found M+=558.0212, 560.0178. C25H20ClN2O3 requires 558.0207, 560.0178.

Workup

  1. customprepared
  2. temperaturewas refluxed for 4 h
  3. washThe cooled solution was washed with water

Sources & evidence

ORD record
ord-aadb4706b7a04a7f8223ac521ce2756f
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Reaction notes

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