Trimethylsilyl cyanide → HCID 67097250, compound

HRID 1698716Notes

Reaction equation

HRID 1698716 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:25]2[O:24][CH2:23][CH2:22][CH2:21][O:20][C:19]=2[C:18]([O:26][CH3:27])=[CH:17][C:16]=1[CH:28]=O.C[Si]([C:34]#[N:35])(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:25]2[O:24][CH2:23][CH2:22][CH2:21][O:20][C:19]=2[C:18]([O:26][CH3:27])=[CH:17][C:16]=1[CH:28]([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:34]#[N:35]

Participants

6

Reactant 4

HCID 82115Trimethylsilyl cyanideHCID 2733225Ytterbium triflateHCID 181881764-(5-Methyl-1,2,4-oxadiazol-3-yl)anilineHCID 59516960HCID 59516960, compound

Product 1

HCID 67097250HCID 67097250, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

After adding 185 mg of 4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamine, 239 mg of 6-fluoro-9-methoxy-3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-carbaldehyde, 250 mg of MS3A and 0.28 ml of trimethylsilyl cyanide to a solution of 65 mg of Yb(OTf)3 in 4 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 (6-fluoro-9-methoxy-3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-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-4fe9d21e27b942a1969c7580fc4a8859
Source dataset
uspto-grants-2012_04
Patent number
US08163787B2

Reaction notes

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