Trimethylsilyl cyanide → HCID 59517233, compound

HRID 1161601Notes

Reaction equation

HRID 1161601 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[CH:6][C:3]=1[CH:4]=O.[NH2:14][C:15]1[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][C:16]=1[F:23].C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Yb+3].C[Si]([C:53]#[N:54])(C)C>C1COCC1>[C:53]([CH:4]([NH:14][C:15]1[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][C:16]=1[F:23])[C:3]1[CH:6]=[C:7]([O:12][CH3:13])[C:8]([O:10][CH3:11])=[CH:9][C:2]=1[F:1])#[N:54]

Participants

6

Reactant 4

HCID 82115Trimethylsilyl cyanideHCID 6035952-Fluoro-4,5-dimethoxybenzaldehydeHCID 2733225Ytterbium triflateHCID 27564314-Amino-3-fluorobenzonitrile

Product 1

HCID 59517233HCID 59517233, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 20 ml of a THF solution containing 1.9 g of 2-fluoro-4,5-dimethoxybenzaldehyde, 1.47 g of 4-amino-3-fluorobenzonitrile [CAS No. 63069-50-1], 6 g of MS3A, 640 mg of Yb(OTf)3, and 4 ml of trimethylsilyl cyanide were added under a nitrogen atmosphere. The resulting mixture was stirred at room temperature overnight and then filtered through celite. The filtrate was concentrated under reduced pressure, and ethyl acetate and water were added to the residue. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and then dried over anhydrous magnesium sulfate. The desiccating agent was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was crudely purified by silica gel column chromatography (ethyl acetate-heptane) and then filtered through NH silica gel to give the title compound (1.0 g) as a light yellow solid.

Workup

  1. filtrationfiltered through celite
  2. concentrationThe filtrate was concentrated under reduced pressure, and ethyl acetate and water
  3. additionwere added to the residue
  4. extractionThe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe desiccating agent was removed by filtration
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe residue was crudely purified by silica gel column chromatography (ethyl acetate-heptane)
  10. filtrationfiltered through NH silica gel

Sources & evidence

ORD record
ord-6c2c10b62db546368dc540e715b38ea9
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

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