Phosphorus oxychloride → 7-Chloro-3-phenyl-imidazo[1,2-a]pyridine-8-carbonitrile

HRID 1627014Notes

Reaction equation

HRID 1627014 reaction equation
O[C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][N:10]=[C:4]2[C:3]=1[C:17]#[N:18].O(Cl)[Cl:20].[P+5].C([O-])(O)=O.[Na+].P(Cl)(Cl)(Cl)=O>CCOCC.CCOC(C)=O>[Cl:20][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][N:10]=[C:4]2[C:3]=1[C:17]#[N:18]

Participants

7

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 178479711HCID 178479711, compoundHCID 178510510HCID 178510510, compound

Product 1

HCID 581038917-Chloro-3-phenyl-imidazo[1,2-a]pyridine-8-carbonitrileYield 33%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of compound D5 (2.3 g, 9.77 mmol) and phosphorus(V) oxychloride (50 ml) was heated at 120° C. for 5 h. After cooling to room temperature the solvents were evaporated in vacuo. The residue thus obtained was carefully poured into a mixture of crushed ice and NaHCO3 (aqueous sat. solution). Then EtOAc was added and the mixture was stirred for 2 h. until complete hydrolysis of the remaining phosphorus oxychloride had occurred. The organic layer was then separated, washed with brine, dried (Na2SO4) and the solvent evaporated in vacuo to give a residue that forms a precipitate upon the addition of Et2O. The solid was filtered off and dried in vacuo to yield compound D6 (0.82 g, 33%) as yellow solid.

Workup

  1. temperatureAfter cooling to room temperature the solvents
  2. customwere evaporated in vacuo
  3. customThe residue thus obtained
  4. customThe organic layer was then separated
  5. washwashed with brine
  6. dry with materialdried (Na2SO4)
  7. customthe solvent evaporated in vacuo
  8. customto give a residue that
  9. filtrationThe solid was filtered off
  10. customdried in vacuo

Sources & evidence

ORD record
ord-627dd06ac0e140b3a60e6bbde86de4ab
Source dataset
uspto-grants-2014_07
Patent number
US08785486B2

Reaction notes

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