Trimethylsilyl cyanide → (5-Fluoro-8-methoxychroman-6-yl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]acetonitrile

HRID 1161442Notes

Reaction equation

HRID 1161442 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:24]([CH:25]=O)=[CH:23][C:22]([O:27][CH3:28])=[C:21]2[C:16]=1[CH2:17][CH2:18][CH2:19][O:20]2.C[Si]([C:33]#[N:34])(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]>C1COCC1>[F:14][C:15]1[C:24]([CH:25]([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:33]#[N:34])=[CH:23][C:22]([O:27][CH3:28])=[C:21]2[C:16]=1[CH2:17][CH2:18][CH2:19][O:20]2

Participants

6

Reactant 4

HCID 82115Trimethylsilyl cyanideHCID 2733225Ytterbium triflateHCID 181881764-(5-Methyl-1,2,4-oxadiazol-3-yl)anilineHCID 595118625-Fluoro-8-methoxychroman-6-carboaldehyde

Product 1

HCID 67097514(5-Fluoro-8-methoxychroman-6-yl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]acetonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

After adding 940 mg of 4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamine, 1.125 g of 5-fluoro-8-methoxychromane-6-carbaldehyde, 1 g of MS3A and 1.43 ml of trimethylsilyl cyanide to a solution of 330 mg of Yb(OTf)3 in 20 ml of THF under a nitrogen atmosphere, 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-methoxychroman-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-c852e18f3c4f4640a652e0394ee25d40
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

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