Trimethylsilyl cyanide → HCID 67097404, compound

HRID 1698712Notes

Reaction equation

HRID 1698712 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.[F:39][C:40]1[C:49]2[O:48][CH2:47][CH2:46][O:45][C:44]=2[C:43]([O:50][CH3:51])=[CH:42][C:41]=1[CH:52]=O.C[Si]([C:58]#[N:59])(C)C>C1COCC1>[F:39][C:40]1[C:49]2[O:48][CH2:47][CH2:46][O:45][C:44]=2[C:43]([O:50][CH3:51])=[CH:42][C:41]=1[CH:52]([NH:38][C:35]1[CH:36]=[CH:37][C:32]([C:29]2[N:28]=[C:27]([CH3:26])[O:31][N:30]=2)=[CH:33][CH:34]=1)[C:58]#[N:59]

Participants

6

Reactant 4

HCID 82115Trimethylsilyl cyanideHCID 2733225Ytterbium triflateHCID 181881764-(5-Methyl-1,2,4-oxadiazol-3-yl)anilineHCID 45121991HCID 45121991, compound

Product 1

HCID 67097404HCID 67097404, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 71 mg of Yb(OTf)3 in 4 ml of THF there were added 204 mg of 4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamine, 247 mg of 5-fluoro-8-methoxy-2,3-dihydrobenzo[1,4]dioxine-6-carbaldehyde, 250 mg of MS3A and 0.30 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 ethyl acetate. The organic layer was concentrated under reduced pressure to give (5-fluoro-8-methoxy-2,3-dihydrobenzo[1,4]dioxin-6-yl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]acetonitrile (crude product).

Workup

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

Sources & evidence

ORD record
ord-88b396f028104651a1d3048f94289118
Source dataset
uspto-grants-2012_04
Patent number
US08163787B2

Reaction notes

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