Sodium Iodide → HCID 66835305, compound

HRID 61922Notes

Reaction equation

HRID 61922 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:9]3[C:10](=[O:29])[C:11]4[C:16]([C:17]([CH3:19])([CH3:18])[C:8]=3[O:7][C:6]=2[CH:30]=1)=[CH:15][C:14]([O:20][CH2:21][C@H:22]1[CH2:26][O:25][C:24]([CH3:28])([CH3:27])[O:23]1)=[CH:13][CH:12]=4.[Na+].[I-:32].CN[C@@H]1CCCC[C@H]1NC>C(OCC)(=O)C.[Cu]I>[CH3:27][C:24]1([CH3:28])[O:23][C@@H:22]([CH2:21][O:20][C:14]2[CH:15]=[C:16]3[C:11](=[CH:12][CH:13]=2)[C:10](=[O:29])[C:9]2[C:5]4[CH:4]=[CH:3][C:2]([I:32])=[CH:30][C:6]=4[O:7][C:8]=2[C:17]3([CH3:18])[CH3:19])[CH2:26][O:25]1

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 66835126HCID 66835126, compound

Product 1

HCID 66835305HCID 66835305, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8857Ethyl AcetateSolvent

Procedure

To 3-bromo-8-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-6,6-dimethyl-6H-benzo[b]naphtho[2,3-d]furan-11-one (15 mg, 0.032 mmol), CuI (6.2 mg, 0.032 mmol), NaI (9.6 mg, 0.064 mmol) and trans-N,N′-dimethylcyclohexane-1,2-diamine (0.01 ml) were added and the mixture was stirred for 48 hrs under nitrogen atmosphere. The reaction solution was diluted with ethyl acetate. The organic layer was washed with saturated brine, and then concentrated under reduced pressure. The resulting residues were purified by silica gel column (ethyl acetate/hexane) to obtain 8-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl methoxy)-3-iodo-6,6-dimethyl-6H-benzo[b]naphtho[2,3-d]furan-11-one (16 mg, 97%), which was then deprotected according to the method of A-14-2 to give the title compound.

Workup

  1. washThe organic layer was washed with saturated brine
  2. concentrationconcentrated under reduced pressure
  3. customThe resulting residues were purified by silica gel column (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-aa01248e7f47418db57a32205b18339c
Source dataset
uspto-grants-2016_09
Patent number
US09440922B2

Reaction notes

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