Phosphorus oxychloride → HCID 15790216, compound

HRID 2399678Notes

Reaction equation

HRID 2399678 reaction equation
[Cl:1][C:2]1[C:7]2[CH:8]=[CH:9][N+:10]([O-])([C:11]3[C:16]([Cl:17])=[CH:15][C:14]([C:18]([F:21])([F:20])[F:19])=[CH:13][N:12]=3)[C:6]=2[CH:5]=[CH:4][N:3]=1.C(=O)(O)[O-].[Na+].P(Cl)(Cl)([Cl:30])=O>>[Cl:17][C:16]1[C:11]([N:10]2[C:6]3[CH:5]=[C:4]([Cl:30])[N:3]=[C:2]([Cl:1])[C:7]=3[CH:8]=[CH:9]2)=[N:12][CH:13]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:15]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 86748984HCID 86748984, compound2×

Product 1

HCID 15790216HCID 15790216, compound

Procedure

4 -chloro-1-(3-chloro-5-trifluoromethylpyridin-2-yl) pyrrolo[3,2-c]pyridine N-oxide (Compound 4, 1.2 g, 3.4 mmol) was heated in phosphorus oxychloride (20 ml) under reflux for 18 hours. The mixture was cooled to room temperature, poured into ice-water, and the mixture made neutral by addition of solid sodium bicarbonate. The resulting mixture was extracted with dichloromethane, and the organic extracts combined, dried over magnesium sulfate, filtered and the filtrate evaporated in vacuo. The residue was further purified by flash column chromatography on silica gel to give 1-(3-chloro-5-trifluoromethylpyridin-2-yl)-4,6-dichloropyrrolo[3,2-c]pyridine (0.24 g) as a colorless oil.

Workup

  1. temperatureunder reflux for 18 hours
  2. extractionThe resulting mixture was extracted with dichloromethane
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customthe filtrate evaporated in vacuo
  6. customThe residue was further purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-a832761c86d44242a0b842c37ecd711c
Source dataset
uspto-grants-1995_09
Patent number
US05451566

Reaction notes

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