Iodine → HCID 86651927, compound

HRID 1685128Notes

Reaction equation

HRID 1685128 reaction equation
[CH3:1][O:2][C:3]1[CH:35]=[C:34]([O:36][CH3:37])[CH:33]=[CH:32][C:4]=1[CH2:5][N:6]1[C:14](=O)[C:13]2[C:8](=[CH:9][C:10]([N+:28]([O-:30])=[O:29])=[C:11]([NH:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][C:19]=3[O:26][CH3:27])[CH:12]=2)[C:7]1=O.CO.C(N(CC)CC)C.II>O1CCCC1.C(O)(=O)C>[CH3:27][O:26][C:19]1[CH:20]=[C:21]([O:24][CH3:25])[CH:22]=[CH:23][C:18]=1[CH2:17][NH:16][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][C:10]=1[N+:28]([O-:30])=[O:29])[CH2:7][N:6]([CH2:5][C:4]1[CH:32]=[CH:33][C:34]([O:36][CH3:37])=[CH:35][C:3]=1[O:2][CH3:1])[CH2:14]2

Participants

7

Reactant 4

HCID 807IodineHCID 887MethanolHCID 8471TriethylamineHCID 67027811HCID 67027811, compound

Product 1

HCID 86651927HCID 86651927, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-(2,4-dimethoxybenzyl)-5-(2,4-dimethoxybenzylamino)-6-nitroisoindoline-1,3-dione T-02 (6.1 g, 12 mmol) in anhydrous tetrahydrofuran (50 mL) cooled in an ice bath was added borane dimethyl sulfide complex (10 M, 36 mL, 360 mmol) in a dropwise manner. The reaction mixture was heated under reflux for 4 hours. The reaction mixture was cooled in an ice bath and methanol (75 mL) was added in a dropwise manner. To the reaction mixture were added triethylamine (6 mL), acetic acid (9 mL) and a solution of iodine (1 g) in anhydrous tetrahydrofuran (5 mL). The reaction mixture was stirred at room temperature overnight. Solvent was removed under reduced pressure. The crude product was diluted with ethyl acetate. The organic layer was washed with 1 N sodium hydroxide solution, water and saturated brine. The organic layer was dried over sodium sulfate. Solvent was evaporated under reduced pressure. The crude product was purified by flash chromatography to afford the desired N,2-bis(2,4-dimethoxybenzyl)-6-nitroisoindolin-5-amine T-03 (2.7 g, 5.6 mmol).

Workup

  1. additionwas added borane dimethyl sulfide complex (10 M, 36 mL, 360 mmol) in a dropwise manner
  2. temperatureThe reaction mixture was heated
  3. temperatureunder reflux for 4 hours
  4. temperatureThe reaction mixture was cooled in an ice bath
  5. customSolvent was removed under reduced pressure
  6. additionThe crude product was diluted with ethyl acetate
  7. washThe organic layer was washed with 1 N sodium hydroxide solution, water and saturated brine
  8. dry with materialThe organic layer was dried over sodium sulfate
  9. customSolvent was evaporated under reduced pressure
  10. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-fa17e1ab15db4e648433b9ee2b398da4
Source dataset
uspto-grants-2012_04
Patent number
US08148363B2

Reaction notes

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