Sodium Iodide → 3-bromo-6-iodo-4H-thieno[3,2-b]pyrrole-5-carboxylic acid methyl ester

HRID 1811690

Reaction equation

HRID 1811690 reaction equation
ClN1C(=O)CCC1=O.[I-:9].[Na+].[CH3:11][O:12][C:13]([C:15]1[NH:19][C:18]2[C:20]([Br:23])=[CH:21][S:22][C:17]=2[CH:16]=1)=[O:14].[O-]S([O-])=O.[Na+].[Na+]>CC(C)=O>[CH3:11][O:12][C:13]([C:15]1[NH:19][C:18]2[C:20]([Br:23])=[CH:21][S:22][C:17]=2[C:16]=1[I:9])=[O:14]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 24437Sodium SulfiteHCID 31398ChlorosuccinimideHCID 44118324Methyl 3-bromo-4H-thieno[3,2-b]pyrrole-5-carboxylate

Product 1

HCID 583104013-bromo-6-iodo-4H-thieno[3,2-b]pyrrole-5-carboxylic acid methyl esterYield 68%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent3×

Procedure

To a solution of N-chlorosuccinimide (12 mmol) in acetone (25 mL) was added dropwise a solution of sodium iodide (12 mmol) in acetone (80 mL). 3-Bromo-4H-thieno[3,2-b]pyrrole-5-carboxylic acid methyl ester (10 mmol) in acetone (80 mL) was then added portionwise into the reaction mixture. After 1 hr of stirring, the reaction was poured into a solution of Na2SO3 10% and extracted with AcOEt. Organic phases were washed with brine, dried over Na2SO4, filtered, and evaporated. The residue was purified by silica gel chromatography to give compound 69 as a yellowish solid in 68% yield. 1H NMR (CDCl3, 400 MHz) δ (ppm) 3.96 (s, 3H), 7.26 (s, 1H), 9.22 (s, 1H).

Workup

  1. extractionextracted with AcOEt
  2. washOrganic phases were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-5951585aa8da42bcaca075ac8e9ac31a
Source dataset
uspto-grants-2013_01
Patent number
US08362068B2

Linked notes

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