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

HRID 1189555Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1189555
[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]

Komponenten

7

Edukt 3

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

Produkt 1

HCID 58310969ethyl 2-(3-cyano-2,4-dimethyl-5-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetateAusbeute 44,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-3378e88baa064e45874072963c8313e3
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08674115B2

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