S,S-dimethylmethanesulfinyl iodide → ethyl 9-bromo-5H-spiro[benzo[2,3]oxepino[4,5-d]thiazole-4,2'-oxirane]-2-carboxylate

HRID 575293노트

반응식

HRID 575293 반응식
CS(I)(C)(C)=O.[CH3:7][C:8]([O-:11])([CH3:10])[CH3:9].[K+].[Br:13][C:14]1[CH:33]=[CH:32][C:17]2[O:18]CC(=O)C3[S:25][C:24]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[N:23][C:22]=3[C:16]=2[CH:15]=1>ClCCl>[Br:13][C:14]1[CH:33]=[CH:32][C:17]2[O:18][CH2:7][C:8]3([C:10]4[S:25][C:24]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[N:23][C:22]=4[C:16]=2[CH:15]=1)[CH2:9][O:11]3

참가 물질

5

반응물 3

HCID 2723795S,S-dimethylmethanesulfinyl iodideHCID 23665647Potassium tert-butoxideHCID 86693324Ethyl 9-bromo-4-oxo-4,5-dihydrobenzo[2,3]oxepino[4,5-d]thiazole-2-carboxylate

생성물 1

HCID 86693323ethyl 9-bromo-5H-spiro[benzo[2,3]oxepino[4,5-d]thiazole-4,2'-oxirane]-2-carboxylate수율 48%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Into a 100-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen was placed a solution of S,S-dimethylmethanesulfinyl iodide (1.15 g, 5.23 mmol, 1.60 equiv), t-BuOK (4 mL, 1.20 equiv) in dichloromethane (5 mL) at room temperature After 30 minutes a solution of ethyl 9-bromo-4-oxo-4,5-dihydrobenzo[2,3]oxepino[4,5-d]thiazole-2-carboxylate (1.2 g, 3.26 mmol, 1.00 equiv) in dichloromethane (10 mL) was added slowly. The resulting solution was stirred for 5 h at room temperature, quenched with water, extracted with dichloromethane, dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified by a silica gel column with ethyl acetate/petroleum ether (1:19) to give 600 mg (48%) of the titled compound as a off-white solid; LC-MS 382,384[M+H]+.

후처리

  1. customInto a 100-mL 3-necked round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. customat room temperature
  4. customAfter 30 minutes
  5. additionwas added slowly
  6. customquenched with water
  7. extractionextracted with dichloromethane
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under vacuum
  10. customThe residue was purified by a silica gel column with ethyl acetate/petroleum ether (1:19)

출처 및 근거

ORD 기록
ord-026c435b8af84c57b5123d4c49c51426
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09034866B2

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