Trimethylsilyl cyanide → (8-methoxy-4H-benzo[1,3]dioxin-6-yl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]acetonitrile

HRID 1161405Notes

Reaction equation

HRID 1161405 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[C:25]2[O:24][CH2:23][O:22][CH2:21][C:20]=2[CH:19]=[C:18]([CH:26]=O)[CH:17]=1.C[Si]([C:32]#[N:33])(C)C>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]>[CH3:14][O:15][C:16]1[C:25]2[O:24][CH2:23][O:22][CH2:21][C:20]=2[CH:19]=[C:18]([CH:26]([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:32]#[N:33])[CH:17]=1

Participants

6

Reactant 3

HCID 82115Trimethylsilyl cyanideHCID 132668188-methoxy-4H-benzo[1,3]dioxine-6-carbaldehydeHCID 181881764-(5-Methyl-1,2,4-oxadiazol-3-yl)aniline

Product 1

HCID 59517220(8-methoxy-4H-benzo[1,3]dioxin-6-yl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]acetonitrile

Reagents, catalysts & solvents 2

HCID 2733225Ytterbium triflateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3.5 g of Yb(OTf)3 in 250 ml of THF there were added 9.8 g of 4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamine, 10.8 g of 8-methoxy-4H-benzo[1,3]dioxine-6-carbaldehyde, 10 g of MS3A and 15 ml of trimethylsilyl cyanide under a nitrogen atmosphere, and the mixture was stirred overnight at room temperature. The reaction mixture was filtered through celite, and the celite was washed with 1000 ml of ethyl acetate. The organic layer was concentrated under reduced pressure to give the title compound (29.2 g, crude product) as a light yellow solid.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washthe celite was washed with 1000 ml of ethyl acetate
  3. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3420033a73fa49a2919973822abf8fd5
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

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