HCID 22144789, compound → HCID 22144785, compound

HRID 1824951Notes

Reaction equation

HRID 1824951 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH3:22])[CH2:10][C:11]1[C:19]2[O:18][CH:17]=[C:16](Br)[C:15]=2[CH:14]=[C:13]([F:21])[CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cu][C:24]#[N:25]>CN(C)C=O.[Cu]I>[C:1]([O:5][C:6]([NH:8][CH:9]([CH3:22])[CH2:10][C:11]1[C:19]2[O:18][CH:17]=[C:16]([C:24]#[N:25])[C:15]=2[CH:14]=[C:13]([F:21])[CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 22144789HCID 22144789, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 22144785HCID 22144785, compoundYield 6%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 0.20 gm (0.54 mMol) N-tert-butoxycarbonyl 1-(3-bromo-5-fluorobenzofur-7-yl)-2-aminopropane, 0.95 gm (5 mMol) copper(I) iodide, and 0.43 gm (4.78 mMol) copper(I) cyanide in 10 mL dimethylformamide was purged with nitrogen for 15 minutes. The mixture was then heated at 120° C. An additional equivalent of copper(I) iodide and copper(I) cyanide were added and the reaction continued at 120° C. for about 16 hours. After cooling to room temperature the reaction mixture was diluted with dichloromethane and then silica gel was added. The solvents were removed under reduced pressure and the dry silica gel remaining was loaded on the top of a silica gel column. The column was then eluted with a gradient of hexane containing from 17% to 20% ethyl acetate. Fractions containing product were combined and concentrated under reduced pressure to provide 0.010 gm (6%) of the desired compound.

Workup

  1. customwas purged with nitrogen for 15 minutes
  2. additionAn additional equivalent of copper(I) iodide and copper(I) cyanide were added
  3. temperatureAfter cooling to room temperature the reaction mixture
  4. additionwas diluted with dichloromethane
  5. additionsilica gel was added
  6. customThe solvents were removed under reduced pressure
  7. washThe column was then eluted with a gradient of hexane containing from 17% to 20% ethyl acetate
  8. additionFractions containing product
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c130a381e2db4c56b0eccc9cc4380b42
Source dataset
uspto-grants-2006_05
Patent number
US07045545B1

Reaction notes

Loading…