Sodium Iodide → HCID 58926149, compound

HRID 383519Notes

Reaction equation

HRID 383519 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5](/[C:6](=[C:12]3\[O:13][C:14]([CH3:24])([CH3:23])[C:15]([N:17]4[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)=[CH:16]\3)/[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[I-:25].[Na+].CN[C@@H]1CCCC[C@H]1NC>[Cu]I.O1CCOCC1>[CH3:23][C:14]1([CH3:24])[O:13]/[C:12](=[C:6]2/[C:7](=[O:11])[NH:8][C:9]3[C:5]/2=[CH:4][CH:3]=[C:2]([I:25])[CH:10]=3)/[CH:16]=[C:15]1[N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 24964164HCID 24964164, compound

Product 1

HCID 58926149HCID 58926149, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To a heavy-wall pressure tube were added (3E)-6-bromo-3-(5,5-dimethyl-4-morpholin-4-ylfuran-2(5H)-ylidene)-1,3-dihydro-2H-indol-2-one (1.6 g, 4.09 mmol), copper (I) iodide (39 mg, 0.20 mmol), sodium iodide (1.23 g, 8.18 mmol), rac-trans-N,N′-dimethylcyclohexane-1,2-diamine (58 mg, 0.41 mmol), and 20 mL of anhydrous 1,4-dioxane. The mixture was purged with nitrogen, sealed and heated in 110° C. bath for 3 days. The mixture was poured into 200 mL of water. The precipitates were filtered, washed with water and dried in vacuo to give the crude product, (3E)-3-(5,5-dimethyl-4-morpholin-4-ylfuran-2(5H)-ylidene)-6-iodo-1,3-dihydro-2H-indol-2-one, as a brown solid. Yield: 2.1 g. This crude material was used in the next step without further purification.

Workup

  1. customThe mixture was purged with nitrogen
  2. customsealed
  3. additionThe mixture was poured into 200 mL of water
  4. filtrationThe precipitates were filtered
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-846358a1b22e4791a39c8cbd913724c1
Source dataset
uspto-grants-2013_02
Patent number
US08367664B2

Reaction notes

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