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

HRID 1698636Notes

Reaction equation

HRID 1698636 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.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[Si]([C:43]#[N:44])(C)C.[CH3:45][O:46][C:47]1[CH:54]=[CH:53][C:50]([CH:51]=O)=[CH:49][C:48]=1[O:55][Si:56]([CH:63]([CH3:65])[CH3:64])([CH:60]([CH3:62])[CH3:61])[CH:57]([CH3:59])[CH3:58]>ClCCl>[CH3:45][O:46][C:47]1[CH:54]=[CH:53][C:50]([CH:51]([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:49][C:48]=1[O:55][Si:56]([CH:57]([CH3:58])[CH3:59])([CH:63]([CH3:64])[CH3:65])[CH:60]([CH3:61])[CH3:62]

Participants

6

Reactant 4

HCID 82115Trimethylsilyl cyanideHCID 2733225Ytterbium triflateHCID 181881764-(5-Methyl-1,2,4-oxadiazol-3-yl)anilineHCID 86617914HCID 86617914, compound

Product 1

HCID 59516995(4-Methoxy-3-triisopropylsilanyloxyphenyl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]acetonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

After adding 3.19 g of 4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamine, 10 g of MS3A, 1.56 g of Yb(OTf)3 and 4.84 ml of trimethylsilyl cyanide to a solution of 5.6 g of 4-methoxy-3-triisopropylsilanyloxybenzaldehyde [CAS No. 179260-96-6] in 98 ml of dichloromethane under a nitrogen atmosphere, the mixture was stirred at room temperature for 12 hours. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane) to give a white solid (5.59 g).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate-heptane)

Sources & evidence

ORD record
ord-4e96569005db46a5a682f6cf37fe5483
Source dataset
uspto-grants-2012_04
Patent number
US08163787B2

Reaction notes

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