4-Aminobenzonitrile → HCID 68422362, compound

HRID 1161521Notes

Reaction equation

HRID 1161521 reaction equation
C[Si]([C:5]#[N:6])(C)C.[F:7][C:8]1[C:17]2[O:16][CH2:15][CH2:14][O:13][C:12]=2[C:11]([O:18][CH3:19])=[CH:10][C:9]=1[CH:20]=O.[NH2:22][C:23]1[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][CH:24]=1>C1COCC1.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:5]([CH:20]([NH:22][C:23]1[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][CH:24]=1)[C:9]1[CH:10]=[C:11]([O:18][CH3:19])[C:12]2[O:13][CH2:14][CH2:15][O:16][C:17]=2[C:8]=1[F:7])#[N:6]

Participants

6

Reactant 3

HCID 133964-AminobenzonitrileHCID 82115Trimethylsilyl cyanideHCID 45121991HCID 45121991, compound

Product 1

HCID 68422362HCID 68422362, compound

Reagents, catalysts & solvents 2

HCID 2733225Ytterbium triflateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

After adding 17 ml of trimethylsilyl cyanide to a suspension of 17.4 g of 5-fluoro-8-methoxy-2,3-dihydrobenzo[1,4]dioxine-6-carbaldehyde (Example 41c), 9.68 g of 4-aminobenzonitrile, 17 g of MS3A, 5 g of Yb(OTf)3 in 400 ml of THF, 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. The residue was washed with an ethyl acetate and heptane mixed solvent to give 4-{[cyano-(5-fluoro-8-methoxy-2,3-dihydrobenzo[1,4]dioxin-6-yl)methyl]amino}benzonitrile (28.01 g).

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
  4. washThe residue was washed with an ethyl acetate and heptane mixed solvent

Sources & evidence

ORD record
ord-e6cdeb0e86d2456280e03aba5fd78567
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

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