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

HRID 2382041노트

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HRID 2382041 반응식
[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]

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 226629314-(5-Fluoro-1h-indol-3-yl)butan-2-oneHCID 178418689HCID 178418689, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-7402002e2a7749bc9ccfeb4170820c99
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08258130B2

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