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

HRID 1161437Notes

Reaction equation

HRID 1161437 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:45]2[CH2:46][O:47][CH2:48][O:49][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:45]2[CH2:46][O:47][CH2:48][O:49][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 595168175-fluoro-8-methoxy-4H-benzo[1,3]dioxine-6-carbaldehyde

Product 1

HCID 67097262(5-fluoro-8-methoxy-4H-benzo[1,3]dioxin-6-yl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]acetonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 45 mg of Yb(OTf)3 in 3 ml of THF there were added 126 mg of 4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamine, 153 mg of 5-fluoro-8-methoxy-4H-benzo[1,3]dioxine-6-carbaldehyde, 0.2 g of MS3A and 192 μl 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 THF. The organic layer was concentrated under reduced pressure to give (5-fluoro-8-methoxy-4H-benzo[1,3]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 THF
  3. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0cd870e949914a9a872bcf820af146bf
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

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