Dimethylformamide → HCID 10473757, compound
Reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:13][CH:14]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:15]([NH:17][CH2:18][C:19]#[N:20])=[O:16])[C:9](F)(F)F)=[CH:4][CH:3]=1.C[N:26]([CH:28]=O)C>CCOC(C)=O.[C-]#N.[Zn+2].[C-]#N>[C:19]([CH2:18][NH:17][C:15](=[O:16])[C@@H:14]([O:13][C@@H:8]([C:9]1[CH:6]=[CH:7][C:2]([C:28]#[N:26])=[CH:3][CH:4]=1)[C:5]1[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1)[CH2:21][CH:22]([CH3:24])[CH3:23])#[N:20]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 2-[1-(4-bromophenyl)-2,2,2-trifluoroethoxy]-N-(cyanomethyl)-4-methylpentanamide from example 69 step 5 (2.03 mmol, 1.0 g) in DMF (2.5 mL), was added zinc cyanide (1.22 mmol, 144 mg) followed by palladium tetrakistriphenylphosphine (0.08 mmol, 92 mg). The mixture was degassed three times via the freeze-thaw method. The mixture was heated at 80° C. overnight. The next day, more zinc cyanide (0.61 mmol, 72 mg) and tetrakistriphenylphosphine (0.04 mmol, 46 mg) were added The mixture was heated at 80° C. overnight. The mixture was cooled to r.t. and diluted with AcOEt (20 mL). The phases were separated and the organic extract was washed with ammonium chloride, brine. The organic layer was dried over anhydrous MgSO4 and concentrated under reduced pressure. Purification: 50:50 (AcOEt:Hex.) gave the title amide.
Workup
- customThe mixture was degassed three times via the freeze-thaw method
- temperaturewas heated at 80° C. overnight
- temperatureThe mixture was cooled to r.t.
- customThe phases were separated
- extractionthe organic extract
- washwas washed with ammonium chloride, brine
- dry with materialThe organic layer was dried over anhydrous MgSO4
- concentrationconcentrated under reduced pressure
- customPurification
Sources & evidence
- ORD record
- ord-c5a5b0476b3943b1bb97dada0cb27b7b
- Source dataset
- uspto-grants-2007_10
- Patent number
- US07279478B2
Reaction notes
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