Sodium Bicarbonate → 7-Chloro-3-(2,2,2-trifluoroethyl)imidazo[1,2-a]pyridine-8-carbonitrile

HRID 1627017Notes

Reaction equation

HRID 1627017 reaction equation
O[C:2]1[CH:7]=[CH:6][N:5]2[C:8]([CH2:11][C:12]([F:15])([F:14])[F:13])=[CH:9][N:10]=[C:4]2[C:3]=1[C:16]#[N:17].O(Cl)[Cl:19].[P+5].C([O-])(O)=O.[Na+]>>[Cl:19][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([CH2:11][C:12]([F:15])([F:14])[F:13])=[CH:9][N:10]=[C:4]2[C:3]=1[C:16]#[N:17]

Participants

4

Reactant 3

HCID 516892Sodium BicarbonateHCID 178479711HCID 178479711, compoundHCID 178510511HCID 178510511, compound

Product 1

HCID 580811367-Chloro-3-(2,2,2-trifluoroethyl)imidazo[1,2-a]pyridine-8-carbonitrile

Conditions

Temperature
130 °C

Procedure

A mixture of compound D9 (1 g, 4.148 mmol) and phosphorus(V) oxychloride (2 ml) was subjected to microwave heating at 130° C. for 15 min. After cooling to room temperature, the solvent was evaporated in vacuo. The residue thus obtained was then treated with NaHCO3 (aqueous sat. solution) and extracted with DCM. The organic layer was separated, dried (MgSO4) and evaporated in vacuo. The crude product was purified by column chromatography (silica gel; Et2O as eluent). The desired fractions were collected and evaporated in vacuo to yield compound D10 (0.6 g, 56%) as yellow solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe solvent was evaporated in vacuo
  3. customThe residue thus obtained
  4. extractionextracted with DCM
  5. customThe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. customevaporated in vacuo
  8. customThe crude product was purified by column chromatography (silica gel; Et2O as eluent)
  9. customThe desired fractions were collected
  10. customevaporated in vacuo
  11. customto yield compound D10 (0.6 g, 56%) as yellow solid

Sources & evidence

ORD record
ord-2edc518de87a4737aa9174ef33903387
Source dataset
uspto-grants-2014_07
Patent number
US08785486B2

Reaction notes

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