Phosphorus oxychloride → 4-(Imidazo[1,5-a]pyridin-5-yl)benzonitrile

HRID 22535Notes

Reaction equation

HRID 22535 reaction equation
C([NH:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:19]3[CH:20]=[N:21][CH:22]=[C:18]3[CH:17]=[CH:16][CH:15]=2)=[CH:10][CH:9]=1)=O)(C)(C)C.P(Cl)(Cl)(Cl)=O>C1(C)C=CC=CC=1>[C:6]([C:8]1[CH:9]=[CH:10][C:11]([C:14]2[N:19]3[CH:20]=[N:21][CH:22]=[C:18]3[CH:17]=[CH:16][CH:15]=2)=[CH:12][CH:13]=1)#[N:5]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 136882255-(p-Tert-butylaminocarbonylphenyl)imidazo[1,5-a]pyridine

Product 1

HCID 136882234-(Imidazo[1,5-a]pyridin-5-yl)benzonitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 0.1 g of 5-(p-tert-butylaminocarbonylphenyl)imidazo[1,5-a]pyridine in 3 ml of toluene is treated with 40 μl of phosphorus oxychloride at 90° for 5 h. The solvent is evaporated and the residue is redissolved in 30 ml of chloroform at 0°. An ice-cold ammonium hydroxide solution is added and the organic phase is separated, dried over sodium sulfate and evaporated. The residue is chromatographed on silica with ethyl acetate to yield the title compound, m.p. 117°-118°.

Workup

  1. customThe solvent is evaporated
  2. dissolutionthe residue is redissolved in 30 ml of chloroform at 0°
  3. additionAn ice-cold ammonium hydroxide solution is added
  4. customthe organic phase is separated
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customThe residue is chromatographed on silica with ethyl acetate

Sources & evidence

ORD record
ord-5133b34280fb4e3db6f4eb05c7a91ab6
Source dataset
uspto-grants-1995_06
Patent number
US05428160

Reaction notes

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