Ethanol → (6-Bromo-5-fluoro-1-methyl-1H-indol-3-yl)-oxo-acetic acid ethyl ester

HRID 222472노트

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HRID 222472 반응식
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[CH3:11])=[CH:4][C:3]=1[F:12].[C:13](Cl)(=[O:17])[C:14](Cl)=[O:15].ClCCl.[CH3:22][CH2:23][OH:24]>CCOCC.CCOC(C)=O>[CH2:23]([O:24][C:13](=[O:17])[C:14]([C:6]1[C:5]2[C:9](=[CH:10][C:2]([Br:1])=[C:3]([F:12])[CH:4]=2)[N:8]([CH3:11])[CH:7]=1)=[O:15])[CH3:22]

참가 물질

7

반응물 4

HCID 702EthanolHCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 591406636-bromo-5-fluoro-1-methyl-1H-indole

생성물 1

HCID 59140635(6-Bromo-5-fluoro-1-methyl-1H-indol-3-yl)-oxo-acetic acid ethyl ester수율 59%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

To a solution of 6-bromo-5-fluoro-1-methyl-1H-indol (0.23 g, 1.00 mmol) in Et2O (15.0 mL) cooled to 0° C. a 2.0 M solution of oxalyl chloride in dichloromethane (0.56 mL, 5.00 mmol) was added dropwise. The reaction was stirred for 0.5 h at 0° C. and allowed to warm to room temperature and stirred overnight. The mixture was cooled to −20° C. and dry EtOH (2 mL) was added. The reaction mixture was diluted with EtOAc, washed with water and brine, dried over Na2SO4 and concentrated. The residue was purified by column chromatography (ethyl acetate-hexane, 1:3) to give the product (0.21 g, 59%). 1H NMR (CDCl3, 300 MHz,): 1.43 (t, J=7.2 Hz, 3H), 3.82 (s, 3H), 4.40 (t, J=7.2 Hz, 2H), 7.47 (d, J=5.4 Hz, 1H), 8.08 (d, J=9.0 Hz, 1H), 8.30 (s, 1H).

후처리

  1. additionwas added dropwise
  2. temperatureto warm to room temperature
  3. stirringstirred overnight
  4. temperatureThe mixture was cooled to −20° C.
  5. washwashed with water and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography (ethyl acetate-hexane, 1:3)

출처 및 근거

ORD 기록
ord-89f956f6a09b479396fb2ac55250b04a
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207216B2

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