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

HRID 1811690

반응식

HRID 1811690 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 180Acetone용매3회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-5951585aa8da42bcaca075ac8e9ac31a
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362068B2

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