Dimethylformamide → 6-cyano-N-[2-ethyl-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6-methylphenyl]-2-naphthamide

HRID 70803Notes

Reaction equation

HRID 70803 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([NH:14][C:15]1[C:20]([CH3:21])=[CH:19][C:18]([C:22]([F:31])([C:27]([F:30])([F:29])[F:28])[C:23]([F:26])([F:25])[F:24])=[CH:17][C:16]=1[CH2:32][CH3:33])=[O:13])[CH:6]=[CH:5]2.[CH3:34][N:35](C)C=O>C(OCC)(=O)C.[C-]#N.[Zn+2].[C-]#N.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:34]([C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([NH:14][C:15]1[C:20]([CH3:21])=[CH:19][C:18]([C:22]([F:31])([C:23]([F:26])([F:25])[F:24])[C:27]([F:30])([F:28])[F:29])=[CH:17][C:16]=1[CH2:32][CH3:33])=[O:13])[CH:6]=[CH:5]2)#[N:35]

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 866729626-Bromo-N-[2-ethyl-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6-methylphenyl]-2-naphthamide

Product 1

HCID 866729616-cyano-N-[2-ethyl-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6-methylphenyl]-2-naphthamideYield 9%

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

6-Bromo-N-[2-ethyl-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6-methylphenyl]-2-naphthamide (0.49 g) was dissolved in N,N-dimethylformamide (4 ml), and deaeration was carried out three times under argon atmosphere (i.e., the reaction solution was de-pressurized to 20 mmHg and brought back to atmospheric pressure under argon atmosphere). Zinc cyanide (0.07 g) and tetrakis (triphenylphosphine) palladium(0) (0.11 g) were added thereto and stirred with heating at 80° C. for 7 hours under argon atmosphere. After cooling to room temperature, the reaction solution was diluted with ethyl acetate, and washed with water and saturated brine. The organic phase was dried over anhydrous magnesium sulfate. The drying agent (anhydrous magnesium sulfate) was removed by filtration and the solvent was distilled off under the reduced pressure. The residue was purified by silica gel chromatography to obtain 6-cyano-N-[2-ethyl-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6-methylphenyl]-2-naphthamide (0.04 g, yield 9%).

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with water and saturated brine
  3. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  4. customThe drying agent (anhydrous magnesium sulfate) was removed by filtration
  5. distillationthe solvent was distilled off under the reduced pressure
  6. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-5ec451366f62494f9c118ec98fe33e9b
Source dataset
uspto-grants-2014_09
Patent number
US08822691B2

Reaction notes

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