Sodium Iodide → Methyl 2-(5-methyl-6-(4-(methylsulfonyl)benzyl)-6H-thieno[2,3-b]pyrrol-4-yl)acetate

HRID 422578노트

반응식

HRID 422578 반응식
[H-].[Na+].[CH3:3][C:4]1[NH:8][C:7]2[S:9][CH:10]=[CH:11][C:6]=2[C:5]=1[CH2:12][C:13]([O:15][CH3:16])=[O:14].Cl[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=1.[I-].[Na+]>CN(C=O)C.CCOC(C)=O>[CH3:3][C:4]1[N:8]([CH2:18][C:19]2[CH:20]=[CH:21][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:23][CH:24]=2)[C:7]2[S:9][CH:10]=[CH:11][C:6]=2[C:5]=1[CH2:12][C:13]([O:15][CH3:16])=[O:14]

참가 물질

7

반응물 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 1235301-(Chloromethyl)-4-methanesulfonylbenzeneHCID 12468203HCID 12468203, 화합물

생성물 1

HCID 57826938Methyl 2-(5-methyl-6-(4-(methylsulfonyl)benzyl)-6H-thieno[2,3-b]pyrrol-4-yl)acetate수율 59.6%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

Sodium hydride (0.014 g, 0.583 mmol) was added to a solution of methyl 2-(5-methyl-6H-thieno[2,3-b]pyrrol-4-yl)acetate (0.109 g, 0.52 mmol) in DMF (5 mL) at 0° C. The mixture was stirred 1 h at 0° C. before sequential addition of the 1-(chloromethyl)-4-(methylsulfonyl)benzene (0.156 g, 0.762 mmol) and sodium iodide (0.0935 g, 0.624 mmol). The reaction mixture was allowed to warm up to ambient temperature over 4 h. EtOAc was added and the resulting solution washed with water. The layers were separated and the organic solution was dried over MgSO4, filtered and concentrated under reduced pressure. The crude material was purified by chromatography on silica gel (heptane/EtOAc: 80/20 to 50/50) to give the title compound (0.117 g, 59.6%): LC/MS (Table 1, Method b) Rt=2.45 min; MS m/z 395 (M+NH4)+.

후처리

  1. washthe resulting solution washed with water
  2. customThe layers were separated
  3. dry with materialthe organic solution was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was purified by chromatography on silica gel (heptane/EtOAc: 80/20 to 50/50)

출처 및 근거

ORD 기록
ord-fdbdfc15828a4b37a3fad1f15149f653
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101645B2

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