Iodine → HCID 67975081, compound

HRID 1502427Notes

Reaction equation

HRID 1502427 reaction equation
[Br:1][C:2]1[C:3]([CH3:11])=[C:4]([Cl:10])[C:5]([CH:8]=[O:9])=[N:6][CH:7]=1.[OH-:12].[K+].II.S([O-])([O-])(=O)=S.[Na+].[Na+].[CH3:23]O>>[Br:1][C:2]1[C:3]([CH3:11])=[C:4]([Cl:10])[C:5]([C:8]([O:12][CH3:23])=[O:9])=[N:6][CH:7]=1

Participants

6

Reactant 5

HCID 807IodineHCID 887Methanol3×HCID 14797Potassium HydroxideHCID 24477Sodium ThiosulfateHCID 86674975HCID 86674975, compound

Product 1

HCID 67975081HCID 67975081, compoundYield 88%

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of 5-bromo-3-chloro-4-methyl-pyridine-2-carbaldehyde (102 mg; 0.43501 mmol) in methanol (4 mL) was sequentially added a solution of potassium hydroxide (105 mg; 1.87149 mmol) in methanol (2 mL) and (dropwise) a solution of iodine (229 mg; 0.898 mmol) in methanol (4 mL). The reaction mixture was stirred at 0° C. for 2 hours, and then a 10% aqueous solution of sodium thiosulfate was added dropwise until the disappearance of the brown color. The reaction mixture was partitioned between ethyl acetate and water, and the organic layer dried with brine and magnesium sulfate, filtered, and evaporated in vacuo to yield 101.8 mg (88%) of the title compound which was carried forward without further purification. LCMS (ESI): M+H=264.0; 1H NMR (400 MHz, DMSO) δ 8.72 (s, 1H), 3.91 (s, 3H), 2.54 (s, 3H).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. dry with materialthe organic layer dried with brine and magnesium sulfate
  3. filtrationfiltered
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-aa3ed836156941b282e7070e928c5de5
Source dataset
uspto-grants-2015_12
Patent number
US09206175B2

Reaction notes

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