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

HRID 1161432Notes

Reaction equation

HRID 1161432 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-22d49e6f00194e769147f293efeb0dd0
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

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