Methyl iodide → HCID 69586595, compound

HRID 723071Notes

Reaction equation

HRID 723071 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([S:23][CH3:24])=[C:8]([S:10]([C:13]2[CH:21]=[C:20]([Br:22])[C:16]3[N:17]=[CH:18][NH:19][C:15]=3[CH:14]=2)(=[O:12])=[O:11])[CH:9]=1)=[O:4].CI.[C:27]([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([S:23][CH3:24])=[C:8]([S:10]([C:13]2[CH:21]=[C:20]([Br:22])[C:16]3[N:17]=[CH:18][N:19]([CH3:27])[C:15]=3[CH:14]=2)(=[O:11])=[O:12])[CH:9]=1)=[O:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 58700468HCID 58700468, compound

Product 1

HCID 69586595HCID 69586595, compoundYield 19.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(7-bromo-3H-benzoimidazole-5-sulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid methyl ester (as prepared in Example 38, step e) (100 mg, 0.22 mmol) in dimethylformamide (2 mL) was added MeI (13.9 μL, 0.22 mmol) and K2CO3 (61.8 mg, 0.45 mmol), then stirred overnight at room temperature. The solvents were removed in vacuo and the residue was diluted with ethyl acetate (100 mL). The ethyl acetate layer was washed with water (15 mL) and brine (25 mL), and dried over MgSO4. The solvent was removed in vacuo to afford 20 mg (19%) of 4-(7-bromo-3-methyl-3H-benzoimidazole-5-sulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid methyl ester and 4-(7-bromo-1-methyl-1H-benzoimidazole-5-sulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid methyl ester as a mixture. This mixture was used directly in the following step.

Workup

  1. customThe solvents were removed in vacuo
  2. additionthe residue was diluted with ethyl acetate (100 mL)
  3. washThe ethyl acetate layer was washed with water (15 mL) and brine (25 mL)
  4. dry with materialdried over MgSO4
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-541044e42488483b9eeae831006be7ac
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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