Trimethylsilyl cyanide → (7-Methoxy-2,3-dihydrobenzofuran-5-yl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]acetonitrile

HRID 1698682Notes

Reaction equation

HRID 1698682 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].[CH3:26][C:27]1[O:31][N:30]=[C:29]([C:32]2[CH:37]=[CH:36][C:35]([NH2:38])=[CH:34][CH:33]=2)[N:28]=1.[CH3:39][O:40][C:41]1[C:49]2[O:48][CH2:47][CH2:46][C:45]=2[CH:44]=[C:43]([CH:50]=O)[CH:42]=1.C[Si]([C:56]#[N:57])(C)C>C1COCC1>[CH3:39][O:40][C:41]1[C:49]2[O:48][CH2:47][CH2:46][C:45]=2[CH:44]=[C:43]([CH:50]([NH:38][C:35]2[CH:36]=[CH:37][C:32]([C:29]3[N:28]=[C:27]([CH3:26])[O:31][N:30]=3)=[CH:33][CH:34]=2)[C:56]#[N:57])[CH:42]=1

Participants

6

Reactant 4

HCID 82115Trimethylsilyl cyanideHCID 2733225Ytterbium triflateHCID 181881764-(5-Methyl-1,2,4-oxadiazol-3-yl)anilineHCID 223438017-Methoxy-2,3-dihydrobenzofuran-5-carbaldehyde

Product 1

HCID 67096962(7-Methoxy-2,3-dihydrobenzofuran-5-yl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]acetonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 426 mg of Yb(OTf)3 in 30 ml of THF there were added 1.2 g of 4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamine, 1.22 g of 7-methoxy-2,3-dihydrobenzofuran-5-carbaldehyde [CAS No. 363185-46-0], 1 g of MS3A and 1.9 ml of trimethylsilyl cyanide under a nitrogen atmosphere, and the mixture was stirred at room temperature. The reaction mixture was filtered through celite, and the celite was washed with 100 ml of ethyl acetate. The organic layer was concentrated under reduced pressure to give a crude product of (7-methoxy-2,3-dihydrobenzofuran-5-yl)-[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 100 ml of ethyl acetate
  3. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-28499abc2f2e4b6ea070269fe5531b3f
Source dataset
uspto-grants-2012_04
Patent number
US08163787B2

Reaction notes

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