Iodobenzene → HCID 71623195, compound

HRID 1048858Notes

Reaction equation

HRID 1048858 reaction equation
[C:1]1([C@H:11]([N:13]([CH2:21][CH:22]2[O:27][CH2:26][C:25](=[O:28])[NH:24][CH2:23]2)[C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.I[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.[Cu](I)I>[C:16]([O:15][C:14](=[O:20])[N:13]([C@@H:11]([C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)[CH3:12])[CH2:21][CH:22]1[O:27][CH2:26][C:25](=[O:28])[N:24]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:23]1)([CH3:17])([CH3:19])[CH3:18]

Participants

6

Reactant 3

HCID 11575IodobenzeneHCID 62657Potassium Phosphate, TribasicHCID 68310884HCID 68310884, compound

Product 1

HCID 71623195HCID 71623195, compoundYield 104.4%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

tert-Butyl ((R)-1-(naphthalen-1-yl)ethyl)((5-oxomorpholin-2-yl)methyl)carbamate (300 mg, 0.78 mmol) (Intermediate-9), iodobenzene (104 μL, 0.93 mmol), potassium phosphate (330 mg, 1.56 mmol), copper iodide (14.8 mg, 0.078 mmol) and N,N′-dimethylaminoethane (17 μL, 0.15 mmol) were added in 1,4-dioxane. The reaction mixture was heated to 110° C. and further stirred overnight at the same temperature. After reaction completion the reaction mixture was concentrated and the residue was purified through silica gel column chromatography (ethyl acetate/hexane=1/4) to obtain the title compound (375 mg) as an oil. m/z 461.08

Workup

  1. customAfter reaction completion the reaction mixture
  2. concentrationwas concentrated
  3. customthe residue was purified through silica gel column chromatography (ethyl acetate/hexane=1/4)

Sources & evidence

ORD record
ord-aa12bd29f44844b091a5d626a012ebfd
Source dataset
uspto-grants-2016_07
Patent number
US09382216B2

Reaction notes

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