Ethyl bromoacetate → ethyl 2-(3-cyano-2,4-dimethyl-5-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetate

HRID 1189555노트

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HRID 1189555 반응식
[CH3:1][C:2]1[NH:3][C:4]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[S:17]([N:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)(=[O:19])=[O:18])=[C:5]([CH3:9])[C:6]=1[C:7]#[N:8].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34]>CCCC[N+](CCCC)(CCCC)CCCC.[I-].CN(C=O)C.C(OCC)(=O)C>[C:7]([C:6]1[C:5]([CH3:9])=[C:4]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[S:17]([N:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)(=[O:19])=[O:18])[N:3]([CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[C:2]=1[CH3:1])#[N:8]

참가 물질

7

반응물 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 583109832,4-dimethyl-5-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrole-3-carbonitrile

생성물 1

HCID 58310969ethyl 2-(3-cyano-2,4-dimethyl-5-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetate수율 44.7%

시약·촉매·용매 3

HCID 67553Tetrabutylammonium Iodide촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
60 °C

실험 절차

A mixture of 2,4-dimethyl-5-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrole-3-carbonitrile (513.6 mg, 1.495 mmol), TBAI (55.2 mg, 0.150 mmol), cesium carbonate (1462 mg, 4.49 mmol), and ethyl bromoacetate (250 μl, 2.243 mmol) in DMF (7.5 ml) was heated at 60° C. for 4 hours. The mixture was diluted in ethyl acetate (100 ml) and washed with water (50 ml×3). The organic layer was dried, filtered, and evaporated to give an oil. This oil was purified by column chromatography (0 to 40% ethyl acetate in hexanes) to give ethyl 2-(3-cyano-2,4-dimethyl-5-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetate (286.9 mg, 0.668 mmol, 44.7% yield). 1H NMR (CDCl3/400 MHz) δ (ppm) 7.92-7.88 (m, 1H), 7.44-7.38 (m, 1H), 7.35-7.29 (m, 1H), 6.96-6.92 (m, 1H), 4.36 (s, 2H), 4.28 (s, 2H), 3.94 (q, 2H), 3.38-3.30 (m, 4H), 2.27 (s, 3H), 2.13 (s, 3H), 1.98-1.92 (m, 4H), 1.11 (t, 3H). MS m/z: 430.3 (M+1).

후처리

  1. washwashed with water (50 ml×3)
  2. customThe organic layer was dried
  3. filtrationfiltered
  4. customevaporated
  5. customto give an oil
  6. customThis oil was purified by column chromatography (0 to 40% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-3378e88baa064e45874072963c8313e3
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08674115B2

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