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

HRID 468623ノート

反応式

HRID 468623 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 86670635(R)-ethyl 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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
70 °C

実験手順

Cesium carbonate (1.77 g, 5.44 mmol) was added to a suspension of 5-fluoro-4-iodopyridin-2(1H)-one (1.00 g, 4.2 mmol) and ethyl (2R)-4-bromo-2-methyl-2-(methylsulfonyl)butanoate (1.56 g, 5.44 mmol) in anhydrous THF (45 mL). The reaction was heated to 70° C. and stirred at this temperature overnight. The reaction was quenched with water (100 mL) and extracted with EtOAc (2×100 mL). The combined organics were washed with brine (100 mL), dried (MgSO4), filtered, and concentrated. The crude product was purified via flash chromatography using a Varian SF15-24 g column and an eluent of EtOAc in n-heptane (30-80%) to afford the title compound as a yellow residue (691 mg, 37%). MS (LCMS) m/z 446.0 (M+1). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.36 (t, 3H) 1.75 (s, 3H) 2.37-2.57 (m, 2H) 3.10 (s, 3H) 3.83-4.02 (m, 1H) 4.16-4.37 (m, 3H) 7.15 (d, 1H) 7.20 (d, J=3.32 Hz, 1H).

後処理

  1. customThe reaction was quenched with water (100 mL)
  2. extractionextracted with EtOAc (2×100 mL)
  3. washThe combined organics were washed with brine (100 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified via flash chromatography

出典と根拠

ORDレコード
ord-96a70edcd95e4eb484fa297a3b05eb6b
出典データセット
uspto-grants-2014_01
特許番号
US08624034B2

反応ノート

読み込み中…