Cesium carbonate → Ethyl (2R)-4-(5-fluoro-4-iodo-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanoate

HRID 84293ノート

反応式

HRID 84293 の反応式
C(=O)([O-])[O-].[Cs+].[Cs+].[F:7][C:8]1[C:9]([I:15])=[CH:10][C:11](=[O:14])[NH:12][CH:13]=1.Br[CH2:17][CH2:18][C:19]([CH3:29])([S:25]([CH3:28])(=[O:27])=[O:26])[C:20]([O:22][CH2:23][CH3:24])=[O:21]>C1COCC1>[F:7][C:8]1[C:9]([I:15])=[CH:10][C:11](=[O:14])[N:12]([CH2:17][CH2:18][C@@:19]([CH3:29])([S:25]([CH3:28])(=[O:27])=[O:26])[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:13]=1

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 706645935-Fluoro-4-iodopyridin-2-olHCID 86670634Ethyl 4-bromo-2-methyl-2-(methylsulfonyl)butanoate

生成物 1

HCID 67249679Ethyl (2R)-4-(5-fluoro-4-iodo-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanoate収率 34.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Cesium carbonate (2.01 g, 6.16 mmol) was added to a solution of the 5-fluoro-4-iodopyridin-2(1H)-one (491 mg, 2.06 mmol) and ethyl 4-bromo-2-methyl-2-(methylsulfonyl)butanoate (767 mg, 2.67 mmol in THF (30 mL). The resulting suspension was heated to reflux and stirred at this temperature overnight. The reaction was filtered through celite (−1 inch), and the filter pad was washed with ethyl acetate (2×30 ml). The combined filtrates were concentrated and the crude was purified via flash chromatography on an Analogix SF15-12g column and an eluant of ethyl acetate in heptane (30-100%) to afford the title compound as a white gum (319 mg, 34.9%). LC-MS m/z 446.0 (M+1). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.35 (t, J=7.12 Hz, 3 H) 1.75 (s, 3 H) 2.40-2.58 (m, 2 H) 3.10 (s, 3 H) 3.87-3.99 (m, 1 H) 4.16-4.25 (m, 1H) 4.29 (q, J=7.22 Hz, 2 H) 7.15 (d, J=5.85 Hz, 1 H) 7.20 (d, J=3.32 Hz, 1 H).

後処理

  1. temperatureThe resulting suspension was heated
  2. temperatureto reflux
  3. filtrationThe reaction was filtered through celite (−1 inch)
  4. washthe filter pad was washed with ethyl acetate (2×30 ml)
  5. concentrationThe combined filtrates were concentrated
  6. customthe crude was purified via flash chromatography on an Analogix SF15-12g column

出典と根拠

ORDレコード
ord-52a6807c855f4c59aa4098d0c33dfd7e
出典データセット
uspto-grants-2014_09
特許番号
US08846933B2

反応ノート

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