Trimethylsilyl cyanide → (2-Cyano-5-{[cyano-(2-fluoro-4,5-dimethoxyphenyl)methyl]amino}benzyl) carbamic Acid t-Butyl Ester

HRID 1157960Notes

Reaction equation

HRID 1157960 reaction equation
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:26]([O:30][C:31](=[O:43])[NH:32][CH2:33][C:34]1[CH:39]=[C:38]([NH2:40])[CH:37]=[CH:36][C:35]=1[C:41]#[N:42])([CH3:29])([CH3:28])[CH3:27].[F:44][C:45]1[CH:52]=[C:51]([O:53][CH3:54])[C:50]([O:55][CH3:56])=[CH:49][C:46]=1[CH:47]=O.C[Si]([C:61]#[N:62])(C)C>O.C(OCC)(=O)C.C1COCC1>[C:26]([O:30][C:31](=[O:43])[NH:32][CH2:33][C:34]1[CH:39]=[C:38]([NH:40][CH:47]([C:61]#[N:62])[C:46]2[CH:49]=[C:50]([O:55][CH3:56])[C:51]([O:53][CH3:54])=[CH:52][C:45]=2[F:44])[CH:37]=[CH:36][C:35]=1[C:41]#[N:42])([CH3:29])([CH3:27])[CH3:28]

Participants

8

Reactant 4

HCID 82115Trimethylsilyl cyanideHCID 6035952-Fluoro-4,5-dimethoxybenzaldehydeHCID 2733225Ytterbium triflateHCID 59511863(5-Amino-2-cyanobenzyl)carbamic acid t-butyl ester

Product 1

HCID 25232592(2-Cyano-5-{[cyano-(2-fluoro-4,5-dimethoxyphenyl)methyl]amino}benzyl) carbamic Acid t-Butyl EsterYield 85.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of Yb(OTf)3(0.124 g) and THF (5 mL) there were added (5-amino-2-cyanobenzyl)carbamic acid t-butyl ester (Example (1g))(0.494 g), 2-fluoro-4,5-dimethoxybenzaldehyde (0.368 g), MS3A (1 g) and trimethylsilyl cyanide (533 mg) in that order under a nitrogen atmosphere, and the mixture was stirred at room temperature for 14 hours. Ethyl acetate (100 mL) and water (50 mL) were added to the mixture and filtration was performed with Celite. After sufficiently shaking the mixture, the organic layer was separated off and dried over anhydrous magnesium sulfate. The mixture was filtered to obtain a filtrate, and the solvent in the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane mixture) to obtain the target compound (0.749 g) as a colorless solid.

Workup

  1. stirringAfter sufficiently shaking the mixture
  2. customthe organic layer was separated off
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe mixture was filtered
  5. customto obtain a filtrate
  6. distillationthe solvent in the filtrate was distilled off under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate-heptane mixture)

Sources & evidence

ORD record
ord-2d8894b828794caa8e4aaa262243a1b3
Source dataset
uspto-grants-2010_10
Patent number
US07807690B2

Reaction notes

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