Trimethylsilyl cyanide → HCID 59517170, compound

HRID 1698622Notes

Reaction equation

HRID 1698622 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.[F:14][C:15]1[C:22]([O:23][Si:24]([CH:31]([CH3:33])[CH3:32])([CH:28]([CH3:30])[CH3:29])[CH:25]([CH3:27])[CH3:26])=[CH:21][C:20]([O:34][CH3:35])=[CH:19][C:16]=1[CH:17]=O.C[Si]([C:40]#[N:41])(C)C.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]>ClCCl.C(OCC)(=O)C>[F:14][C:15]1[C:22]([O:23][Si:24]([CH:31]([CH3:32])[CH3:33])([CH:28]([CH3:29])[CH3:30])[CH:25]([CH3:27])[CH3:26])=[CH:21][C:20]([O:34][CH3:35])=[CH:19][C:16]=1[CH:17]([NH:13][C:10]1[CH:11]=[CH:12][C:7]([C:4]2[N:3]=[C:2]([CH3:1])[O:6][N:5]=2)=[CH:8][CH:9]=1)[C:40]#[N:41]

Participants

7

Reactant 4

HCID 82115Trimethylsilyl cyanideHCID 2733225Ytterbium triflateHCID 181881764-(5-Methyl-1,2,4-oxadiazol-3-yl)anilineHCID 59511839HCID 59511839, compound

Product 1

HCID 59517170HCID 59517170, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

After adding 5.47 g of 4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamine, 10.2 g of 2-fluoro-5-methoxy-3-triisopropylsilanyloxybenzaldehyde, 10 g of MS3A and 6.2 ml of trimethylsilyl cyanide to a solution of 1.94 g of Yb(OTf)3 in 100 ml of dichloromethane under a nitrogen atmosphere, the mixture was stirred for 3 days at room temperature. Ethyl acetate was added to the reaction mixture, and washing was performed with water. The organic layer was dried over anhydrous magnesium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane) to give the title compound (9.01 g) as a light yellow solid.

Workup

  1. washwashing
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationThe desiccating agent was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate-heptane)

Sources & evidence

ORD record
ord-d2279bb4bf2a49e19d4b98f51f11509d
Source dataset
uspto-grants-2012_04
Patent number
US08163787B2

Reaction notes

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