4-Aminobenzonitrile → HCID 67504429, compound

HRID 1161517Notes

Reaction equation

HRID 1161517 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.C[Si]([C:14]#[N:15])(C)C.[F:16][C:17]1[C:24]([O:25][Si:26]([CH:33]([CH3:35])[CH3:34])([CH:30]([CH3:32])[CH3:31])[CH:27]([CH3:29])[CH3:28])=[CH:23][C:22]([O:36][CH3:37])=[CH:21][C:18]=1[CH:19]=O>C1COCC1.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:14]([CH:19]([NH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1)[C:18]1[CH:21]=[C:22]([O:36][CH3:37])[CH:23]=[C:24]([O:25][Si:26]([CH:27]([CH3:28])[CH3:29])([CH:33]([CH3:34])[CH3:35])[CH:30]([CH3:31])[CH3:32])[C:17]=1[F:16])#[N:15]

Participants

6

Reactant 3

HCID 133964-AminobenzonitrileHCID 82115Trimethylsilyl cyanideHCID 59511839HCID 59511839, compound

Product 1

HCID 67504429HCID 67504429, compound

Reagents, catalysts & solvents 2

HCID 2733225Ytterbium triflateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

After adding 18 g of 4-aminobenzonitrile, 50 g of MS3A, 6.65 g of Yb(OTf)3 and 28.6 ml of trimethylsilyl cyanide to a solution of 50.04 g of 2-fluoro-5-methoxy-3-triisopropylsilanyloxybenzaldehyde (Example 3b) in 300 ml of THF under a nitrogen atmosphere, the mixture was stirred at room temperature for 4 hours. The reaction mixture was filtered through celite, and the celite was washed with ethyl acetate. The organic layer was concentrated under reduced pressure. The residue was dissolved in ethyl acetate, and the organic layer was washed with water and saturated brine and then dried over anhydrous sodium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The obtained solid was suspended in ethyl acetate-heptane (1:2) and the solid was filtered to give 4-{[cyano-(2-fluoro-5-methoxy-3-triisopropylsilanyloxyphenyl)methyl]amino}benzonitrile (59.32 g).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washthe celite was washed with ethyl acetate
  3. concentrationThe organic layer was concentrated under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washthe organic layer was washed with water and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationThe desiccating agent was filtered off
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. filtrationthe solid was filtered

Sources & evidence

ORD record
ord-132f012014b347559c6d83771f33933e
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

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