HCID 58392432, compound → HCID 58392094, compound

HRID 561439Notes

Reaction equation

HRID 561439 reaction equation
[F:1][C:2]1([F:34])[O:6][C:5]2[CH:7]=[CH:8][C:9]([CH:11]([C:22]3[C:30]4[C:25](=[C:26]([CH2:31][S:32][CH3:33])[CH:27]=[CH:28][CH:29]=4)[NH:24][CH:23]=3)[CH:12]3C(=O)O[C:15](C)([CH3:19])[O:14][C:13]3=[O:21])=[CH:10][C:4]=2[O:3]1>N1C=CC=CC=1.C(O)C.[Cu]>[F:34][C:2]1([F:1])[O:6][C:5]2[CH:7]=[CH:8][C:9]([CH:11]([C:22]3[C:30]4[C:25](=[C:26]([CH2:31][S:32][CH3:33])[CH:27]=[CH:28][CH:29]=4)[NH:24][CH:23]=3)[CH2:12][C:13]([O:14][CH2:15][CH3:19])=[O:21])=[CH:10][C:4]=2[O:3]1

Participants

5

Reactant 1

HCID 58392432HCID 58392432, compound

Product 1

HCID 58392094HCID 58392094, compound

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 702EthanolSolventHCID 1049PyridineSolvent

Procedure

17 mg (271 μmol) of copper powder were added to a solution of 2.66 g (5.43 mmol) of the compound from Example 97A in 10 ml of pyridine and 2 ml of ethanol. The reaction mixture was heated under reflux for 4 h. It was concentrated, and the crude product was purified firstly by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate gradient) and then by preparative HPLC (mobile phase: acetonitrile/water gradient). 1.73 g (74% of theory) of the title compound were obtained.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 4 h
  3. concentrationIt was concentrated
  4. customthe crude product was purified firstly by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate gradient)

Sources & evidence

ORD record
ord-ad9fdb94f25a41c49ada9fd2b5315077
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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