Phosphorus oxychloride → 4-Chloro-7-iodo-2-methylthiazolo[4,5-c]pyridine

HRID 1443115Notes

Reaction equation

HRID 1443115 reaction equation
[I:1][C:2]1[C:3]2[S:11][C:10]([CH3:12])=[N:9][C:4]=2[C:5](=O)[NH:6][CH:7]=1.O=P(Cl)(Cl)[Cl:15]>>[Cl:15][C:5]1[C:4]2[N:9]=[C:10]([CH3:12])[S:11][C:3]=2[C:2]([I:1])=[CH:7][N:6]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 685382577-Iodo-2-methyl-5H-thiazolo[4,5-c]pyridin-4-one

Product 1

HCID 768504784-Chloro-7-iodo-2-methylthiazolo[4,5-c]pyridine

Procedure

7-Iodo-2-methyl-5H-thiazolo[4,5-c]pyridin-4-one (880 mg, 3.01 mmol) was suspended in POCl3 (8.25 ml, 90.4 mmol) and refluxed for 4 hrs. The black reaction mixture was evaporated and poured as a dichloromethane solution in ice water. The aqueous layer was neutralized with solid NaHCO3 to pH 7 and extracted three times with dichloromethane. The combined organic extracts were dried with magnesium sulfate, filtered and evaporated. The crude product was purified by chromatography on silica gel (dichloromethane/methanol 100:0->95:5 gradient). The desired product was obtained as a light yellow solid (280 mg, 30%), MS: m/e=311.0 (M+H+).

Workup

  1. temperaturerefluxed for 4 hrs
  2. customThe black reaction mixture
  3. customwas evaporated
  4. additionpoured as a dichloromethane solution in ice water
  5. extractionextracted three times with dichloromethane
  6. dry with materialThe combined organic extracts were dried with magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude product was purified by chromatography on silica gel (dichloromethane/methanol 100:0->95:5 gradient)

Sources & evidence

ORD record
ord-b2045eb1d6a540f7a59604198367d3ce
Source dataset
uspto-grants-2010_02
Patent number
US07659401B2

Reaction notes

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