HCID 86680890, compound → HCID 67995547, compound

HRID 2042932Notes

Reaction equation

HRID 2042932 reaction equation
[C:1]([O:4][C@H:5]1[C@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@H:8]([C:19]2[CH:24]=[CH:23][C:22](Br)=[C:21]([CH2:26][C:27]3[S:28][C:29]([C:32]4[O:33][CH:34]=[CH:35][CH:36]=4)=[CH:30][N:31]=3)[CH:20]=2)[O:7][C@@H:6]1[CH2:37][O:38][C:39](=[O:41])[CH3:40])(=[O:3])[CH3:2].[Cu][C:43]#[N:44]>CN1C(=O)CCC1>[C:1]([O:4][C@H:5]1[C@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@H:8]([C:19]2[CH:24]=[CH:23][C:22]([C:43]#[N:44])=[C:21]([CH2:26][C:27]3[S:28][C:29]([C:32]4[O:33][CH:34]=[CH:35][CH:36]=4)=[CH:30][N:31]=3)[CH:20]=2)[O:7][C@@H:6]1[CH2:37][O:38][C:39](=[O:41])[CH3:40])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 86680890HCID 86680890, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 67995547HCID 67995547, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

The bromide 58 (300 mg, 0.46 mmol) was added to a microwave reaction tube containing copper(I) cyanide (124 mg, 1.38 mmol) in NMP. The capped reaction tube was placed in a microwave reactor and the mixture irradiated at 230° C. for 30 min. After dilution with EtOAc, the organic layer was washed with 15% NH4OH solution prior to drying over anhydrous MgSO4. After filtration and concentration under reduced pressure, the residue was purified by silica column chromatography to provide the cyanide 59 (208 mg, 76%) as a white solid. MH+597.

Workup

  1. customThe capped reaction tube
  2. customwas placed in a microwave reactor
  3. customthe mixture irradiated at 230° C. for 30 min
  4. washAfter dilution with EtOAc, the organic layer was washed with 15% NH4OH solution
  5. dry with materialto drying over anhydrous MgSO4
  6. filtrationAfter filtration and concentration under reduced pressure
  7. customthe residue was purified by silica column chromatography

Sources & evidence

ORD record
ord-ca1e9041bd0a4202bfea9f05a71719ff
Source dataset
uspto-grants-2013_11
Patent number
US08586550B2

Reaction notes

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