HCID 22292777, compound → HCID 22292795, compound

HRID 2389423Notes

Reaction equation

HRID 2389423 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[C:14](Br)[C:15]([O:17][CH3:18])=[CH:16][C:8]=2[CH2:7][CH2:6]1)=[O:4].[C:22]([Cu])#[N:23]>CN(C)C=O.O>[F:1][C:2]([F:21])([F:20])[C:3]([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[C:14]([C:22]#[N:23])[C:15]([O:17][CH3:18])=[CH:16][C:8]=2[CH2:7][CH2:6]1)=[O:4]

Participants

5

Reactant 2

HCID 22292777HCID 22292777, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 22292795HCID 22292795, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of N-trifluoroacetyl-8-bromo-7-methoxy-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (18 mg, 0.05 mmol) in dimethylformamide (1 mL) was treated with CuCN (20 mg, 0.24 mmol) and the mixture was microwaved at 200 C. for 0.5 hours. The product mixture was diluted with water (5 mL), extracted twice with EtOAc (5 mL), the combined organic phases were washed with brine (5 mL), dried with Na2SO4 and concentrated. Flash chromatography (35% EtOAc in hexane, silica) resulted in 10 mg of a clear oil. MS calculated for C15H15F3N2O2+H: 313, observed: 313.

Workup

  1. customthe mixture was microwaved at 200 C
  2. extractionextracted twice with EtOAc (5 mL)
  3. washthe combined organic phases were washed with brine (5 mL)
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f7f91f08a4974b8db9cc1dc64d1504c7
Source dataset
uspto-grants-2012_09
Patent number
US08273734B1

Reaction notes

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