Trimethylsilyl cyanide → HCID 67505491, compound

HRID 1161585Notes

Reaction equation

HRID 1161585 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].[F:36][C:37]1[C:44]([O:45][Si:46]([CH:53]([CH3:55])[CH3:54])([CH:50]([CH3:52])[CH3:51])[CH:47]([CH3:49])[CH3:48])=[CH:43][C:42]([O:56][CH3:57])=[CH:41][C:38]=1[CH:39]=O.C[Si]([C:62]#[N:63])(C)C>C1COCC1>[C:62]([CH:39]([NH:10][C:8]1[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([F:1])[CH:9]=1)[C:38]1[CH:41]=[C:42]([O:56][CH3:57])[CH:43]=[C:44]([O:45][Si:46]([CH:47]([CH3:48])[CH3:49])([CH:53]([CH3:54])[CH3:55])[CH:50]([CH3:51])[CH3:52])[C:37]=1[F:36])#[N:63]

Participants

6

Reactant 4

HCID 82115Trimethylsilyl cyanideHCID 2733225Ytterbium triflateHCID 27834134-Amino-2-fluorobenzonitrileHCID 59511839HCID 59511839, compound

Product 1

HCID 67505491HCID 67505491, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Fluoro-4-aminobenzonitrile [CAS No. 53312-80-4] (1.02 g), MS3A (7 g), and Yb(OTf)3 (465 mg) were added to 30 ml of a THF solution containing 2.45 g of 2-fluoro-5-methoxy-3-triisopropylsilanyloxybenzaldehyde (Example (3b)) under a nitrogen atmosphere. The resulting mixture was stirred at room temperature for 2 hours, and then 1.1 ml of trimethylsilyl cyanide was added thereto. The mixture was stirred at room temperature for 3 days. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane) to give 4-{[cyano-(2-fluoro-5-methoxy-3-triisopropylsilanyloxyphenyl)methyl]amino}-2-fluorobenzonitrile (2.05 g) as a yellow oil.

Workup

  1. stirringThe mixture was stirred at room temperature for 3 days
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate-heptane)

Sources & evidence

ORD record
ord-5a82f2289ec8469194af24afccf7598b
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

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