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

HRID 422578ノート

反応式

HRID 422578 の反応式
[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]

参加物

7

反応物 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 1235301-(Chloromethyl)-4-methanesulfonylbenzeneHCID 12468203HCID 12468203、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-fdbdfc15828a4b37a3fad1f15149f653
出典データセット
uspto-grants-2012_01
特許番号
US08101645B2

反応ノート

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