Potassium Phosphate, Tribasic → HCID 86670638、化合物

HRID 468626

反応式

HRID 468626 の反応式
[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH3:9][S:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.[F:20][C:21]1[C:22](I)=[CH:23][C:24](=[O:40])[N:25]([CH2:27][CH2:28][C@@:29]([CH3:39])([S:35]([CH3:38])(=[O:37])=[O:36])[C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH:26]=1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O1CCOCC1>[F:20][C:21]1[C:22]([C:14]2[CH:15]=[CH:16][C:11]([S:10][CH3:9])=[CH:12][CH:13]=2)=[CH:23][C:24](=[O:40])[N:25]([CH2:27][CH2:28][C@@:29]([CH3:39])([S:35]([CH3:38])(=[O:36])=[O:37])[C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH:26]=1

参加物

6

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 27339594-(Methylthio)phenylboronic acidHCID 67249679Ethyl (2R)-4-(5-fluoro-4-iodo-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanoate

生成物 1

HCID 86670638HCID 86670638、化合物収率 99%

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
60 °C

実験手順

1,4-Dioxane (10 ml) and 3 M aq K3PO4 (1.12 mL, 3.3 mmol) was added to a flask containing [4-(methylthio)phenyl]boronic acid (0.283 g, 1.68 mmol), Pd(dppf)Cl2 (82 mg, 0.112 mmol) and ethyl (2R)-4-(5-fluoro-4-iodo-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanoate, T2, (500 mg, 1.12 mmol) that was previously flushed with nitrogen. The mixture was heated to 60° C. and stirred at this temperature for 1 h. The reaction mixture was diluted with EtOAc and washed with water. The organics were dried (MgSO4), filtered, and concentrated. The crude product was purified via flash chromatography on a 40 g silica column and an eluent of EtOAc in n-heptane (0-100%) to afford the title compound as a gum (492 mg, 99%). MS (LCMS) m/z 442.1 (M+1). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.17-1.27 (m, 3H) 1.74 (s, 3H) 2.38-2.61 (m, 5H) 3.09 (s, 3H) 3.88-4.02 (m, 1H) 4.17-4.32 (m, 3H) 6.57 (d, J=7.61 Hz, 1H) 7.21-7.34 (m, 3H) 7.37-7.48 (m, 2H).

後処理

  1. customwas previously flushed with nitrogen
  2. additionThe reaction mixture was diluted with EtOAc
  3. washwashed with water
  4. dry with materialThe organics were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified via flash chromatography on a 40 g silica column

出典と根拠

ORDレコード
ord-7d71d2b1f0b54776bb385564c195f335
出典データセット
uspto-grants-2014_01
特許番号
US08624034B2

関連ノート

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