Trimethylsilyl cyanide → [3,4-Dimethoxy-5-(1-triisopropylsilanyloxyethyl)phenyl][4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]acetonitrile

HRID 1698667Notes

Reaction equation

HRID 1698667 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=2)[N:3]=1.[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:21]=[C:22]([CH:26]([O:28][Si:29]([CH:36]([CH3:38])[CH3:37])([CH:33]([CH3:35])[CH3:34])[CH:30]([CH3:32])[CH3:31])[CH3:27])[C:23]=1[O:24][CH3:25])[CH:19]=O.C[Si]([C:43]#[N:44])(C)C.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]>ClCCl>[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:19]([NH:13][C:10]2[CH:11]=[CH:12][C:7]([C:4]3[N:3]=[C:2]([CH3:1])[O:6][N:5]=3)=[CH:8][CH:9]=2)[C:43]#[N:44])[CH:21]=[C:22]([CH:26]([O:28][Si:29]([CH:33]([CH3:35])[CH3:34])([CH:36]([CH3:38])[CH3:37])[CH:30]([CH3:32])[CH3:31])[CH3:27])[C:23]=1[O:24][CH3:25]

Participants

6

Reactant 4

HCID 82115Trimethylsilyl cyanideHCID 2733225Ytterbium triflateHCID 181881764-(5-Methyl-1,2,4-oxadiazol-3-yl)anilineHCID 595171933,4-Dimethoxy-5-(1-triisopropylsilanyloxyethyl)benzaldehyde

Product 1

HCID 67097068[3,4-Dimethoxy-5-(1-triisopropylsilanyloxyethyl)phenyl][4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]acetonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

After adding 0.99 g of 4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamine, 2.607 g of 3,4-dimethoxy-5-(1-triisopropylsilanyloxyethyl)benzaldehyde, 1.7 g of MS3A and 1.6 ml of trimethylsilyl cyanide to a solution of 350 mg of Yb(OTf)3 in 14 ml of dichloromethane under a nitrogen atmosphere, the mixture was stirred at room temperature for 2 days. The reaction mixture was filtered through celite, and the celite was washed with ethyl acetate. The organic layer was concentrated under reduced pressure to give a crude product of [3,4-dimethoxy-5-(1-triisopropylsilanyloxyethyl)phenyl][4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]acetonitrile.

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

Sources & evidence

ORD record
ord-fc87cf7ea46447bea112228498513d67
Source dataset
uspto-grants-2012_04
Patent number
US08163787B2

Reaction notes

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