Trimethylsilyl cyanide → HCID 67503830, compound

HRID 1161523Notes

Reaction equation

HRID 1161523 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=O)[CH:6]=[N:7][C:8]=1[O:9][CH3:10].[CH3:13][C:14]1[O:18][N:17]=[C:16]([C:19]2[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=2)[N:15]=1.C[Si]([C:30]#[N:31])(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]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([NH:25][C:22]2[CH:23]=[CH:24][C:19]([C:16]3[N:15]=[C:14]([CH3:13])[O:18][N:17]=3)=[CH:20][CH:21]=2)[C:30]#[N:31])[CH:6]=[N:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 3

HCID 82115Trimethylsilyl cyanideHCID 141837035,6-Dimethoxypyridine-3-carbaldehydeHCID 181881764-(5-Methyl-1,2,4-oxadiazol-3-yl)aniline

Product 1

HCID 67503830HCID 67503830, compound

Reagents, catalysts & solvents 2

HCID 2733225Ytterbium triflateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.0 g of 5,6-dimethoxypyridine-3-carbaldehyde [CAS No. 52605-99-9] in 10 ml of THF there were added 1.15 g of 4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamine, 5 g of MS3A and 371 mg of Yb(OTf)3 under a nitrogen atmosphere, and after stirring at room temperature for 2 hours, 4.5 ml of trimethylsilyl cyanide was added and the mixture was stirred at room temperature for 12 hours and 30 minutes. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. A dichloromethane, heptane and ethyl acetate mixed solvent was added and the mixture was filtered to give (5,6-dimethoxypyridin-3-yl)-[4-(5-methyl[1,2,4]oxadiazol-3-yl)phenylamino]acetonitrile (2.19 g) as a white solid.

Workup

  1. stirringthe mixture was stirred at room temperature for 12 hours and 30 minutes
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionA dichloromethane, heptane and ethyl acetate mixed solvent was added
  5. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-1e4a66ddcaf34c31b45982da678b967e
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

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