Veratraldehyde → HCID 67097205, compound

HRID 1161452Notes

Reaction equation

HRID 1161452 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([NH2:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].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].C[Si]([C:40]#[N:41])(C)C.[CH3:42][O:43][C:44]1[CH:45]=[C:46]([CH:49]=[CH:50][C:51]=1[O:52][CH3:53])[CH:47]=O>C1COCC1>[C:40]([CH:47]([NH:10][C:8]1[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([F:1])[CH:9]=1)[C:46]1[CH:49]=[CH:50][C:51]([O:52][CH3:53])=[C:44]([O:43][CH3:42])[CH:45]=1)#[N:41]

Participants

6

Reactant 4

HCID 8419VeratraldehydeHCID 82115Trimethylsilyl cyanideHCID 2733225Ytterbium triflateHCID 27834134-Amino-2-fluorobenzonitrile

Product 1

HCID 67097205HCID 67097205, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

After adding 541 mg of 2-fluoro-4-aminobenzonitrile [CAS No. 53312-80-4], 500 mg of MS3A, 493 mg of Yb(OTf)3 and 1.1 ml of trimethylsilyl cyanide to a solution of 795 mg of 3,4-dimethoxybenzaldehyde in 20 ml of THF under a nitrogen atmosphere, the mixture was stirred at room temperature for 14 hours. 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 a crude product of 4-{[cyano-(3,4-dimethoxyphenyl)methyl]amino}-2-fluorobenzonitrile.

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-ad4539f4aecf46618095835a8233167d
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

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