Trimethylsilyl cyanide → HCID 67096599, compound

HRID 1698707Notes

Reaction equation

HRID 1698707 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:20]2[CH2:21][CH2:22][O:23][C:19]=2[C:18]([O:24][CH3:25])=[CH:17][C:16]=1[CH:26]=O.C[Si]([C:32]#[N:33])(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:20]2[CH2:21][CH2:22][O:23][C:19]=2[C:18]([O:24][CH3:25])=[CH:17][C:16]=1[CH:26]([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:32]#[N:33]

Participants

6

Reactant 4

HCID 82115Trimethylsilyl cyanideHCID 2733225Ytterbium triflateHCID 181881764-(5-Methyl-1,2,4-oxadiazol-3-yl)anilineHCID 59516813HCID 59516813, compound

Product 1

HCID 67096599HCID 67096599, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

After adding 287 mg of 4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamine [CAS No. 10185-68-9], 321 mg of 4-fluoro-7-methoxy-2,3-dihydrobenzofuran-5-carbaldehyde, 300 mg of MS3A and 0.44 ml of trimethylsilyl cyanide to a solution of 102 mg of Yb(OTf)3 in 5 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 (4-fluoro-7-methoxy-2,3-dihydrobenzofuran-5-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-8d2bd09bdca540a2a89fa57b5b8a4d79
Source dataset
uspto-grants-2012_04
Patent number
US08163787B2

Reaction notes

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