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

HRID 222472ノート

反応式

HRID 222472 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-89f956f6a09b479396fb2ac55250b04a
出典データセット
uspto-grants-2012_06
特許番号
US08207216B2

反応ノート

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