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

HRID 1189555ノート

反応式

HRID 1189555 の反応式
[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]

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 67553Tetrabutylammonium Iodide触媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-3378e88baa064e45874072963c8313e3
出典データセット
uspto-grants-2014_03
特許番号
US08674115B2

反応ノート

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