Trimethylsilyl cyanide → HCID 19383044, compound

HRID 2399677Notes

Reaction equation

HRID 2399677 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[N:12]1[C:20]2[CH:19]=[CH:18][N+:17]([O-])=[CH:16][C:15]=2[CH:14]=[CH:13]1.C[Si](C#N)(C)C>C(N(CC)CC)C>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[N:12]1[C:20]2[CH:19]=[CH:18][N:17]=[CH:16][C:15]=2[CH:14]=[CH:13]1

Participants

4

Reactant 2

HCID 82115Trimethylsilyl cyanideHCID 15790217HCID 15790217, compound

Product 1

HCID 19383044HCID 19383044, compoundYield 50.6%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A solution of 1-(2-chloro-4-trifluoromethylphenyl)-pyrrolo[3,2-c]pyridine 5-oxide (3.5 g, 12 mmol) in triethylamine (50 ml) was cooled in an ice-bath and trimethylsilyl cyanide (10.7 ml, 80 mmol) added dropwise. The ice-bath was removed and the mixture stirred for 5 hours. The precipitate was collected and dried to afford 1-(2-chloro-4-trifluoromethylphenyl)pyrrolo[3,2-c]pyridine (1.8g) as a colorless solid, m.p. 160°-161° C.

Workup

  1. customThe ice-bath was removed
  2. customThe precipitate was collected
  3. customdried

Sources & evidence

ORD record
ord-6349bf2e00584b37aeecdf174a040959
Source dataset
uspto-grants-1995_09
Patent number
US05451566

Reaction notes

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