Sodium Iodide → tert-Butyl 6-iodo-3,4-dihydroisoquinoline-2(1H)-carboxylate

HRID 564054Notes

Reaction equation

HRID 564054 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13](Br)[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C)CCN.[I-:25].[Na+]>O1CCOCC1.N.[Cu]I>[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([I:25])[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 5238Sodium IodideHCID 66053N,N-DimethylethylenediamineHCID 49761184tert-Butyl 6-bromo-3,4-dihydroisoquinoline-2(1H)-carboxylate

Product 1

HCID 67006753tert-Butyl 6-iodo-3,4-dihydroisoquinoline-2(1H)-carboxylate

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 222AmmoniaSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To 13.0 g (41.6 mmol) 6-bromo-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester in 42 mL 1,4-dioxane is added 817 mg (4.21 mmol) copper(I)-iodide under argon. After flushing with argon, 0.89 mL (8.33 mmol) N,N-dimethylethylen-diamine and 12.5 g (83.3 mmol) sodium iodide is added at RT. The reaction mixture is stirred 14 h at 110° C., is cooled to RT and is diluted with 5% aqueous ammonia-solution. The layers are separated and the aqueous phase is extracted with EtOAc. The combined organic phase is washed with water and is dried over MgSO4, filtered and the solvent is evaporated to give the product.

Workup

  1. additionis added at RT
  2. temperatureis cooled to RT
  3. customThe layers are separated
  4. extractionthe aqueous phase is extracted with EtOAc
  5. washThe combined organic phase is washed with water
  6. dry with materialis dried over MgSO4
  7. filtrationfiltered
  8. customthe solvent is evaporated
  9. customto give the product

Sources & evidence

ORD record
ord-1c7c9b6e6a75474d9e8152220b8f2718
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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