Sodium Hydroxide → 7-Chloro-2-propyl-thiazolo[5,4-b]pyridine

HRID 607142Notes

Reaction equation

HRID 607142 reaction equation
[CH2:1]([C:4]1[S:5][C:6]2[NH:7][CH:8]=[CH:9][C:10](=O)[C:11]=2[N:12]=1)[CH2:2][CH3:3].P(Cl)(Cl)([Cl:16])=O.[OH-].[Na+]>>[Cl:16][C:10]1[CH:9]=[CH:8][N:7]=[C:6]2[S:5][C:4]([CH2:1][CH2:2][CH3:3])=[N:12][C:11]=12

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 668085072-Propyl-4H-thiazolo[5,4-b]pyridin-7-one

Product 1

HCID 668084877-Chloro-2-propyl-thiazolo[5,4-b]pyridineYield 89%

Procedure

The product of Example 5F (123 mg, 0.6332 mmol) and phosphorous oxychloride (2 mL) were refluxed for 1 hour under a nitrogen atmosphere. The solution was cooled in an ice bath, treated with ice, and the pH adjusted to 7 with 6N aqueous sodium hydroxide. Extracted with methylene chloride (3×50 mL) and dried the combined organic extracts over anhydrous sodium sulfate, filtered and concentrated under vacuum giving the title compound as a brown oil (120 mg, 0.564 mmol, 89%).

Workup

  1. temperatureThe solution was cooled in an ice bath
  2. additiontreated with ice
  3. extractionExtracted with methylene chloride (3×50 mL)
  4. dry with materialdried the combined organic extracts over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-57abe906e36f4eeeaf66848e68592c48
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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