Ammonium Chloride → 4-(5-fluoro-1H-indol-3-yl)-2-methyl-butan-2-ol

HRID 2382041ノート

反応式

HRID 2382041 の反応式
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][C:13](=[O:15])[CH3:14].[CH3:16][Mg+].[Br-].[NH4+].[Cl-]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][C:13]([CH3:16])([OH:15])[CH3:14]

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 226629314-(5-Fluoro-1h-indol-3-yl)butan-2-oneHCID 178418689HCID 178418689、化合物

生成物 1

HCID 685590834-(5-fluoro-1H-indol-3-yl)-2-methyl-butan-2-ol収率 26%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A solution of 4-(5-fluoro-1H-indol-3-yl)-butan-2-one (11.1 g, 54.1 mmol) in THF (200 mL) at 0° C. is treated with MeMgBr (54.1 mL, 3 M in THF, 162.3 mmol) and stirred at 0° C. for 2 h, and warmed to rt overnight. The mixture is then poured over ice, treated with solid NH4Cl (3 g), and extracted with EtOAc (3×120 mL). The combined organic layer is dried (Na2SO4), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 10%-60% EtOAc in heptane to afford 4-(5-fluoro-1H-indol-3-yl)-2-methyl-butan-2-ol (3.07 g, 26%). MS: 222 (M+H); 1H NMR (300 MHz, CDCl3): δ 7.94 (s, NH, 1H), 7.22 (m, 2H), 7.03 (s, 1H), 6.93 (m, 1H), 2.81 (m, 2H), 1.90 (m, 2H), 1.33 (s, 6H).

後処理

  1. temperaturewarmed to rt overnight
  2. additionThe mixture is then poured over ice
  3. extractionextracted with EtOAc (3×120 mL)
  4. dry with materialThe combined organic layer is dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by silica gel chromatography
  8. washeluting with 10%-60% EtOAc in heptane

出典と根拠

ORDレコード
ord-7402002e2a7749bc9ccfeb4170820c99
出典データセット
uspto-grants-2012_09
特許番号
US08258130B2

反応ノート

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