Iodine → HCID 57722482, compound

HRID 2267097Notes

Reaction equation

HRID 2267097 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([C:15]([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)=[O:16])=[CH:13][N:12]=[C:11]([CH:26]=[O:27])[C:10]=1[O:28][CH3:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:30].[K+].II.S([O-])(O)=O.[Na+].[CH3:39]O>O>[CH2:1]([O:8][C:9]1[C:14]([C:15](=[O:16])[NH:17][CH2:18][C:19]2[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=2)=[CH:13][N:12]=[C:11]([C:26]([O:30][CH3:39])=[O:27])[C:10]=1[O:28][CH3:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 807IodineHCID 887Methanol3×HCID 14797Potassium HydroxideHCID 23665763Sodium BisulfiteHCID 57722486HCID 57722486, compound

Product 1

HCID 57722482HCID 57722482, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of the compound 26 (300 mg, 0.761 mmol) in methanol (1 ml) was added a solution of potassium hydroxide (111 mg, 1.99 mmol) in methanol (1 ml) under ice-cooling, and a solution of iodine (251 mg, 1.00 mmol) in methanol (4 ml) was further added, followed by stirring at the same temperature for 1 hour. To the reaction solution were added a 5% aqueous sodium hydrogen sulfite solution and water, and precipitated crystals were collected by filtration. Methyl 4-benzyloxy-5-(4-fluorobenzylcarbamoyl)-3-methoxypyridine-2-carboxylate 27 (275 mg, 85%) was obtained as a colorless crystal.

Workup

  1. temperaturecooling
  2. customprecipitated crystals
  3. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-1b578d5570d44fcd9b81f561c4d344b6
Source dataset
uspto-grants-2010_12
Patent number
US07858788B2

Reaction notes

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